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Journal articles on the topic '[3.3.0]furofuranone'

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Published: 8 June 2024

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1

Peng, Xiao-Shui, Ridge Michael P. Ylagan, Yuk Ming Siu, and Henry N. C. Wong. "Synthesis and Application of [3.3.0]Furofuranone in Total Synthesis." Chemistry - An Asian Journal 10, no. 10 (July 20, 2015): 2070–83. http://dx.doi.org/10.1002/asia.201500288.

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2

Peng, Xiao-Shui, Ridge Michael P. Ylagan, Yuk Ming Siu, and Henry N. C. Wong. "ChemInform Abstract: Synthesis and Application of [3.3.0]Furofuranone in Total Synthesis." ChemInform 46, no. 46 (October 27, 2015): no. http://dx.doi.org/10.1002/chin.201546255.

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3

Kojic, Vesna, Milos Svircev, Sanja Djokic, Ivana Kovacevic, Marko Rodic, Bojana Sreco-Zelenovic, Velimir Popsavin, and Mirjana Popsavin. "Synthesis and antiproliferative activity of new thiazole hybrids with [3.3.0]furofuranone or tetrahydrofuran scaffolds." Journal of the Serbian Chemical Society, no. 00 (2023): 2. http://dx.doi.org/10.2298/jsc221130002k.

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New thiazole hybrids were synthesized and evaluated for their in vitro cytotoxicity against a panel of human malignant cell lines. The key steps in the synthesis of hybrids 3-7 involved the initial condensation of appropriate aldononitriles with cysteine ethyl ester hydrochloride, followed by subsequent treatment of resulting thiazolines with DBU to form the thiazole ring. Bioiso-steres 8 and 14 have been prepared after the stereoselective addition of 2-(tri-methylsilyl)thiazole to the hemiacetals obtained by periodate cleavage of terminal diol functionality in the suitably protected D-glucose derivatives. The obtained analogues showed various antiproliferative activities in the cultures of several tumour cell lines. Hybrid 6 was the most potent in HeLa cells, exhibiting more than 10 and 4 times stronger activity than both leads 1 and 2, respectively. The most active compound in Raji cells was hybrid 12, which was nearly 2-fold more potent than the clinical antitumour drug doxorubicin. All analogues were more potent in A549 cells with respect to lead 1, while compounds 6 and 7 were slightly more active than DOX. Preliminary SAR analysis revealed that the presence of a cinnamate group at the C-3 position in analogues of type 7 increases the activity of resulting molecular hybrids.

4

Ariztia, Julen, Alicia Chateau, Cédric Boura, Claude Didierjean, Sandrine Lamandé-Langle, and Nadia Pellegrini Moïse. "Synthesis of anti-proliferative [3.3.0]furofuranone derivatives by lactonization and functionalization of C-glycosyl compounds." Bioorganic & Medicinal Chemistry 45 (September 2021): 116313. http://dx.doi.org/10.1016/j.bmc.2021.116313.

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5

Rios, María Y., Yordin D. Ocampo-Acuña, M. Ángeles Ramírez-Cisneros, and María E. Salazar-Rios. "Furofuranone Lignans from Leucophyllum ambiguum." Journal of Natural Products 83, no. 5 (April 2, 2020): 1424–31. http://dx.doi.org/10.1021/acs.jnatprod.9b00759.

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6

Swain, Nigel A., Richard C. D. Brown, and Gordon Bruton. "An efficient synthesis of endo,exo-furofuranone derivatives." Chemical Communications, no. 18 (August 13, 2002): 2042–43. http://dx.doi.org/10.1039/b206150c.

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7

Marchand, Patrice A., Norman G. Lewis, and Jaroslav Zajicek. "Oxygen insertion in Sesamumindicum furanofuran lignans. Diastereoselective syntheses of enzyme substrate analogues." Canadian Journal of Chemistry 75, no. 6 (June 1, 1997): 840–49. http://dx.doi.org/10.1139/v97-102.

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The furofuran lignans in sesame seed have an unusual oxygen insertion between their furan and aryl rings. In our continuing investigations on the isolation and characterization of the enzyme(s) involved, the diastereoselective syntheses of various substrate analogues for the oxygen insertion step were developed for future substrate specificity and inhibitor studies. This synthetic strategy also provided entry to so-called furofuranone epoxy-lignans, such as salicifoliol from Bupleurum sp., and acuminatolide from Helichrysum sp. Keywords: furofuran lignans, sesame, epimers, salicifoliol, acuminatolide.

8

Zhang, Wen, Lingzi Li, and Chuang-Chuang Li. "Synthesis of natural products containing highly strained trans-fused bicyclo[3.3.0]octane: historical overview and future prospects." Chemical Society Reviews 50, no. 17 (2021): 9430–42. http://dx.doi.org/10.1039/d0cs01471k.

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Molecules with highly strained trans-fused bicyclo[3.3.0]octanes are very difficult to synthesize. This review provides a systematic and comprehensive discussion on the synthesis of natural products with trans-fused bicyclo[3.3.0]octanes.

9

Yates, Peter, D. Jean Burnell, Vernon J. Freer, and Jeffery F. Sawyer. "Synthesis of cedranoid sesquiterpenes. III. Functionalization at carbon 4." Canadian Journal of Chemistry 65, no. 1 (January 1, 1987): 69–77. http://dx.doi.org/10.1139/v87-012.

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Dimethyl 6,6-dimethyl-5,7-dioxobicyclo[2.2.2]oct-2-ene-2,3-dicarboxylate (8) on irradiation in acetophenone gives dimethyl 6,6-dimethyl-4,7-dioxotricyclo[3.2.1.02,8]octane-1,8-dicarboxylate (13), which on treatment with lithium dimethylcuprate followed by monodecarbomethoxylation gives methyl 4,4-endo-8-trimethyl-3,6-dioxo-cis-bicyclo[3.3.0]octane-1-carboxylate (17). Similar irradiation of dimethyl 4,6,6-trimethyl-5,7-dioxobicyclo[2.2.2]oct-2-ene-2,3-dicarboxylate (24) and its 7,7-ethylenedioxy derivative (25) followed by treatment with DBU and concentrated H2SO4, respectively, gives dimethyl 3-hydroxy-4,4,8-trimethyl-6-oxo-cis-bicyclo[3.3.0]-octa-2,7-diene-1,2-dicarboxylate (30). This, on acetylation, reduction with NaBH4/CeCl3, methanolysis, monodecarbomethoxylation, and hydrogenation, gives methyl endo-6-hydxoxy 4,4-endo-8-trimethyl-3-oxo-cis-bicyclo[3.3.0]octane-1-carboxylate (38), while on reduction with Li/NH3 followed by monodecarbomethoxylation it gives a methyl 6-hydroxy-4,4-exo-8-trimethyl-3-oxo-cis-bicyclo[3.3.0]octane-1-carboxylate (33).

10

Yates, Peter, Rupinder S. Grewal, Peter C. Hayes, and Jeffery F. Sawyer. "Synthesis of cedranoid sesquiterpenes. V. The biotols." Canadian Journal of Chemistry 66, no. 11 (November 1, 1988): 2805–15. http://dx.doi.org/10.1139/v88-434.

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Reduction of dimethyl 3-hydroxy-4,4,8-trimethyl-6-oxo-cis-bicyclo[3.3.0]octa-2,7-diene-1,2-dicarboxylate (8) with lithium and ammonia gives dimethyl 3-hydroxy-4,4,exo-8-trimethyl-6-oxo-cis-bicyclo[3.3.0]oct-2-ene-1,2-dicarboxylate (9), which on acetylation, reduction with sodium borohydride, and methanolysis gives dimethyl 3,exo-6-dihydroxy-4,4,exo-8-trimethyl-cis-bicyclo[3.3.0]oct-2-ene-1,2-dicarboxylate (12). This on 2-decarbomethoxylation followed by treatment with lithium acetylide in the presence of cerium trichloride gives methyl 3-ethynyl-3,exo-6-dihydroxy-4,4,exo-8-trimethyl-cis-bicyclo[3.3.0]octane-1-carboxylate (21), which on hydration, diacetylation, and treatment with tri-n-butyltin hydride and azoisobutyronitrile is converted to methyl exo-6-acetoxy-3-acetyl-4,4,exo-8-trimethyl-cis-bicyclo[3.3.0]octane-1-carboxylate (31). Methanolysis of 31. tert-butyldimethylsilylation, and reaction with potassium tert-butoxide in tert-butyl alcohol gives exo-4-tert-butyldimethylsilyloxy-exo-2,6,6-trimethyl[5.3.11,5]undecane-8,10-dione (35). This on treatment with lithium aluminum hydride followed by oxidation and hydrogenation provides the corresponding 10-deoxo compound, 39. Reaction of this with methyllithium, dehydration, and desilylation with hydrogen fluoride in acetonitrile gives a mixture of (±)-α-biotol (1) and (±)-β-biotol (2); desilylation with hydrogen chloride in methanol gives solely (±)-1.

11

Delamere, C., C. Jakins, and E. Lewars. "Tests for aromaticity applied to the pentalenoquinones A computational study." Canadian Journal of Chemistry 79, no. 10 (October 1, 2001): 1492–504. http://dx.doi.org/10.1139/v01-164.

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Criteria for aromaticity and antiaromaticity were applied to the four pentalenoquinones, 1,2-, 1,5-, 1,4-, and 1,6-pentalenoquinone, i.e., bicyclo[3.3.0]octa-4,6,8-triene-2,3-dione (7a), bicyclo[3.3.0]octa-3,5,8-triene-2,7-dione (7b), bicyclo[3.3.0]octa-1(5),3,7-triene-2,6-dione (7c), and bicyclo[3.3.0]octa-1(5),3,6-triene-2,8-dione (7d). Geometry optimizations and frequency calculations were done with the pBP/DN* DFT method as implemented in Spartan, and single-point HF/3-21G calculations to obtain Löwdin bond orders (Spartan), as well as HF/6-31G* NICS calculations (Gaussian 98) were also carried out. Geometries and bond orders, chemical hardness, and NICS values gave no definite indication of aromatic or antiaromatic character. However, homodesmotic ring-opening reactions to give acyclic analogues indicated that 7a and 7b are nonaromatic (resonance energies 11 and 5 kJ mol1) while 7c and 7d are antiaromatic (resonance energies 83 and 54 kJ mol1). The resonance energies were obtained with the aid of an estimate of the strain energy of the molecules 7 (86 kJ mol1) by a novel extrapolation procedure on hydropentalenes. Calculated pBP/DN* activation energies for DielsAlder reactions with ethyne and ethene placed 7a and 7b in an "unreactive" class similar to 1,3-butadiene and fulvene, and 7c and 7d in a "reactive" class, similar to cyclopentadienone.Key words: aromaticity, pentalenoquinones, DFT, hardness, NICS, homodesmotic, resonance energy, bicyclo[3.3.0]octatrienediones.

12

Guthrie, J. Peter, Roger T. Gallant, and Michael C. Jennings. "Preparation and characterization of bicyclic amide acetals and monothioacetals." Canadian Journal of Chemistry 82, no. 2 (February 1, 2004): 268–78. http://dx.doi.org/10.1139/v03-204.

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We have prepared and characterized new examples of 5-substituted-1-aza-4,6-dioxabicyclo[3.3.0]octanes (bicyclic amide acetals) and examples of the new heterocyclic system, 5-substituted-1-aza-4-oxa-6-thiabicyclo[3.3.0]octanes (bicyclic amide monothioacetals). Detailed analysis of NMR coupling constants and X-ray structure determination for an example of each class of compound established the stereochemistry and conformation of these ring systems.Key words: bicyclic amide acetals, preparation, coupling constants, X-ray structure.

13

Riaz, Muhammad, Nisar Ullah, Arshad Mehmood, Hafiz Rab Nawaz, Abdul Malik, and Nighat Afza. "Furanoid and Furofuranoid Lignans from Daphne oleoides." Zeitschrift für Naturforschung B 55, no. 12 (December 1, 2000): 1216–20. http://dx.doi.org/10.1515/znb-2000-1217.

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Furofuranoid lignan (1) and (2) and furanoid lignan (3) have been isolated from Daphne oleoides and their structures elucidated through chemical and spectroscopic studies as 2-(3'- methoxy-4′-O-α-D-galactopyranosylphenyl)-6-(3″-methoxy-4″-hydroxyphenyl)-3,7-dioxabicyclo[ 3.3.0]octane (1), 2-(3′,5′-dimethoxy-4′-O-a-D-galactopyranosylphenyl)-6-(3″-m ethoxy- 4″-hydroxyphenyl)-3,7-dioxabicyclo[3.3.0]octane (2), and 4,9′-dihydroxy-3,3′-dimethoxy-4′- O-β-D-glucopyranosyl-7′,9-epoxylignan (3). Two known lignans (4) and (5) have also been reported for the first time from this species.

14

Yu, Zhi-Xiang, and Cheng-Hang Liu. "Rh(I)-Catalyzed Intramolecular [3+2] Cycloaddition of trans-2-Allene-Vinylcyclopropanes." Synlett 29, no. 06 (January 18, 2018): 764–68. http://dx.doi.org/10.1055/s-0037-1609199.

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15

Tănase, Constantin I., Constantin Drăghici, and Miron Teodor Caproiu. "New β-ketophosphonates for the synthesis of prostaglandin analogues. 2 Phosphonates with bicyclo[3.3.0]octene and bicyclo[3.3.0]octane scaffolds linked to the β-keto group." New Journal of Chemistry 44, no. 46 (2020): 20405–10. http://dx.doi.org/10.1039/d0nj04594b.

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16

Robertson, Jeremy, and Kiri Stevens. "Pyrrolizidine alkaloids." Nat. Prod. Rep. 31, no. 12 (2014): 1721–88. http://dx.doi.org/10.1039/c4np00055b.

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17

Deslongchamps, Ghislain, Daniel Mink, Paul D. Boyle, and Nina Singh. "Unusual Weiss–Cook condensation of dimethyl 2,3-dioxobutanedioate and dimethyl 3-oxoglutarate." Canadian Journal of Chemistry 72, no. 4 (April 1, 1994): 1162–64. http://dx.doi.org/10.1139/v94-148.

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The Weiss–Cook condensation of dimethyl 2,3-dioxobutanedioate with two equivalents of dimethyl 3-oxoglutarate in aqueous bicarbonate produces an "abnormal" product, pentamethyl cis-3-(carbomethoxymethyl)-3,7-dihydroxy-2-oxabicyclo-[3.3.0]oct-7-ene-1,4,5,6,8-pentacarboxylate 7, whose structure has been determined by X-ray crystallography. Rrapcho decarbomethoxylation (sodium chloride, aqueous dimethyl sulfoxide, 140 °C) of this compound produces dimethyl cis-3,7-dioxobi-cyclo[3.3.0]octane-1,5-dicarboxylate 4 in quantitative yield. These results suggest that compound 7 may be the product of a kinetically controlled reaction pathway involving 4-hydroxypent-2-en-1-one intermediate 5. Heating of 7 in dimethyl sulfoxide may have promoted thermodynamic equilibration to a Weiss–Cook product, which then decarbomethoxylated to produce 4.

18

Krech, Friedrich, Babett Krauss, Adolf Zschunke, and Clemens Mügge. "Cis-1-phosphabicyclo[3.3.0]octan." Zeitschrift für anorganische und allgemeine Chemie 629, no. 9 (August 2003): 1475–76. http://dx.doi.org/10.1002/zaac.200300096.

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19

Gimazetdinov, Airat M., Aidar Z. Al’mukhametov, and Mansur S. Miftakhov. "Development of a new approach for the synthesis of (+)-15-deoxy-Δ^12,14-prostaglandin J₂ methyl ester based on the [2+2]-cycloadduct of 5-trimethylsilylcyclopentadiene and dichloroketene." New Journal of Chemistry 46, no. 14 (2022): 6708–14. http://dx.doi.org/10.1039/d2nj01003h.

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20

Robertson, Jeremy, and Kiri Stevens. "Pyrrolizidine alkaloids: occurrence, biology, and chemical synthesis." Natural Product Reports 34, no. 1 (2017): 62–89. http://dx.doi.org/10.1039/c5np00076a.

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21

Antoniadis, Greg A., Michael T. M. Clements, Sriyawathie Peiris, and J. B. Stothers. "13C magnetic resonance studies. 131. An examination of β-enolization in an unsaturated [3.2.1] system: 3,3-dimethylbicyclo[3.2.1]oct-6-en-2-one." Canadian Journal of Chemistry 65, no. 7 (July 1, 1987): 1557–62. http://dx.doi.org/10.1139/v87-262.

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Under homoenolization conditions (t-BuO−/t-BuOH/185 °C), 3,3-dimethylbicyclo[3.2.1]oct-6-en-2-one (5) is converted into six products through three reaction pathways. The major product, 3,3-dimethylbicyclo[3.3.0]octan-2-one, arises by unidirectional β-enolate rearrangement of 5 to the isomeric unsaturated [3.3.0] ketones, which (a) undergo efficient reduction to 2, by single electron transfer, and (b) suffer Haller–Bauer cleavage to two isomeric 2,2-dimethyl-3-cyclopentenylpropanoic acids. In competition with these processes is the reversible conjugate addition of t-BuO− to 5 to furnish the 6-tert-butoxy derivative, which undergoes β-enolate rearrangement to two isomeric ketones. The structures of these products were established primarily from their 1H and 13C magnetic resonance spectra.

22

Aurich, Hans Günter, and Michael Soeberdt. "Darstellung enantiomerenreiner 3-Oxa-2,7-diazabicyclo[3.3.0]octane und ihre Umwandlung in andere bicyclische Ringsysteme/Preparation of Pure Enantiomeric 3-Oxa-2,7-diazabicyclo[3.3.0]octanes and their Conversion to Other Bicyclic Ring-Systems." Zeitschrift für Naturforschung B 54, no. 1 (January 1, 1999): 87–95. http://dx.doi.org/10.1515/znb-1999-0117.

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Pure Enantiomeric (S)-N-benzylalaninol (R1 = Me) and (S)-N-benzylvalinol (R1 = i-Pr) were allylated with Br-CH2-CH=CR2R3 (R2 = R3 = H; R2 = Ph, R3 = H; R2 = R3 = Ph). Swern oxidation followed by treatment with methylhydroxylamine afforded nitrones 6 (Me- N(O)=CH-CHR1-N(CH2Ph)CH2-CH=CR2R3) which underwent an intramolecular 1,3-dipolar cycloaddition providing 3-oxa-2,7-diazabicyclo[3.3.0]octanes, e.g. (1R,5R,8S)-7-benzyl-2,8- dimethyl-3-oxa-2,7-diazabicyclo[3.3.0]octane 7a (R1 = Me, R2 = R3 = H) and (1R,4R,5R,8S)- 7-benzyl-2,8-dimethyl-4-phenyl-3-oxa-2,7-diazabicyclo[3.3.0]-octane 7b (R1 = Me, R2 = Ph, R3 = H).Reductive ring opening of 7a and 7b afforded the corresponding a-hydroxyalkylated pyrrolidines (9a: R2 = H or 9b: R2 = Ph. resp.). Condensation of these compounds with benzaldehyde yielded a mixture of diastereomeric 4-oxa-2,8-diazabicyclo[4.3.0]- nonanes: 10a/11a (1R,3S,6R,9S)/(1R,3R,6R,9S) R1 = Me, R2 = R3 = H and 10b /lib (1R,3S,5R,6R,9S)/(1R,3R,5R,6R,9S) R1 = Me, R2 = Ph, R3 = H. Pyrrolidine 9b was converted to the mesylate which formed (1R,4S,5R,7S)-3-benzyl-4,6-dimethyl-7-phenyl-3,6-diazabicyclo[3.2.0]heptane 13 along with (4R,5S)-1-benzyl-3,5-dimethyl-4-styryl-imidazolidine 15 upon treatment with sodium hydroxide.

23

Brandstätter, Marco, Nikolas Huwyler, and Erick M. Carreira. "Gold(i)-catalyzed stereoselective cyclization of 1,3-enyne aldehydes by a 1,3-acyloxy migration/Nazarov cyclization/aldol addition cascade." Chemical Science 10, no. 35 (2019): 8219–23. http://dx.doi.org/10.1039/c9sc02828e.

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Optically active 1,3-enyne aldehydes undergo stereoselective, Au-catalyzed conversion to bicyclo[3.3.0]octenones (up to 97% ee, good d.r.) via a domino sequence involving 1,3-acyloxy migration, Nazarov cyclization and an unprecedented aldol addition.

24

Bhat, Bilal A., Showkat Rashid, and Goverdhan Mehta. "Progress in the Total Synthesis of Natural Products Embodying Diverse Furofuranone Motifs: A New Millennium Update." Asian Journal of Organic Chemistry 9, no. 11 (October 13, 2020): 1726–53. http://dx.doi.org/10.1002/ajoc.202000401.

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25

Flippen-Anderson, Judith L., Jeffrey R. Deschamps, Clifford George, and Richard D. Gilardi. "4,4,8,8-Tetranitro-2,6-dioxabicyclo[3.3.0]octane." Acta Crystallographica Section E Structure Reports Online 58, no. 9 (August 23, 2002): o1018—o1020. http://dx.doi.org/10.1107/s1600536802014101.

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26

Baumeister, U., H. Hartung, and F. Krech. "1-Phosphabicyclo[3.3.0]octane 1-sulfide." Acta Crystallographica Section C Crystal Structure Communications 46, no. 4 (April 15, 1990): 634–37. http://dx.doi.org/10.1107/s0108270189008085.

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27

Eberle, Marcel K., Reinhart Keese, and Helen Stoeckli-Evans. "A bicyclo[3.3.0]octan-2-ylcyclopentanone." Acta Crystallographica Section E Structure Reports Online 57, no. 5 (April 30, 2001): o461—o462. http://dx.doi.org/10.1107/s1600536801006808.

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28

Ma, Chenxi, and Anthony F. Hill. "Methimazolyl based diptych bicyclo-[3.3.0]-ruthenaboratranes." Dalton Transactions 48, no. 6 (2019): 1976–92. http://dx.doi.org/10.1039/c8dt04813d.

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The reactions of [RuCl(R)(CO)(PPh₃)₂] (R = CHCHPh, Ph) with Na[H₂B(mt)₂] (mt = N-methyl-2-mercaptoimidazolyl) transiently provide [Ru(R)(CO)(PPh₃){κ³-H,S,S′-H₂B(mt)₂}] which each evolve to the ruthenaboratrane [Ru(CO)(PPh₃)₂{κ³-B,S,S′-BH(mt)₂}](Ru→B)⁸.

29

Xiang, Yuejun, Raymond F. Schinazi, and Kang Zhao. "Synthesis of [3.3.0] bicyclic isoxazolidinyl nucleosides." Bioorganic & Medicinal Chemistry Letters 6, no. 13 (July 1996): 1475–78. http://dx.doi.org/10.1016/s0960-894x(96)00262-4.

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30

Vega, Andrés, Oscar Donoso-Tauda, Andres Ibañez, and Carlos A. Escobar. "Five bicyclo[3.3.0]octa-2,6-dienes." Acta Crystallographica Section C Crystal Structure Communications 64, no. 4 (March 8, 2008): o199—o204. http://dx.doi.org/10.1107/s0108270108004290.

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31

Knotnerus, J., and H. Schilling. "Bicyclanes: V. New syntheses of cis-bicyclo[3.3.0]octane and cis-bicyclo[3.3.0]oct-2-ene." Recueil des Travaux Chimiques des Pays-Bas 83, no. 11 (September 2, 2010): 1185–90. http://dx.doi.org/10.1002/recl.19640831110.

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32

Muhit, Md Abdul, Kaoru Umehara, and Hiroshi Noguchi. "Five furofuranone lignan glucosides from Terminalia citrina inhibit in vitro E 2 -enhanced breast cancer cell proliferation." Fitoterapia 113 (September 2016): 74–79. http://dx.doi.org/10.1016/j.fitote.2016.07.004.

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33

Gund, Machhindra, Martin Déry, and Claude Spino. "Synthesis of carotol using a formal (4+1)-cycloaddition of chiral dialkoxycarbenes." Canadian Journal of Chemistry 96, no. 3 (March 2018): 311–27. http://dx.doi.org/10.1139/cjc-2017-0594.

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We report formal intramolecular (4+1)-cycloadditions of dialkoxycarbenes used in the synthesis of the daucane-type sesquiterpene carotol. We found a chiral dialkoxycarbene capable of diastereoselective formation of a key oxabicyclo[3.3.0]octene adduct. Carotol was synthesized in 14 linear steps from simple starting materials.

34

Grygorenko, Oleksandr, Yevhenii Sokolenko, Eugeniy Ostapchuk, and Artem Artemenko. "An Approach to 3-Oxa-7-azabicyclo[3.3.0]octanes – Bicyclic Morpholine Surrogates." Synthesis 49, no. 14 (April 13, 2017): 3112–17. http://dx.doi.org/10.1055/s-0036-1588785.

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An approach to 3-oxa-7-azabicyclo[3.3.0]octanes, bicyclic morpholine analogues, is reported, which relies on [3+2] cycloaddition of maleic anhydrides or furan-2(5H)-ones and an in situ generated azomethine ylide. The utility of the method was demonstrated on a multigram scale.

35

Tanase, Constantin I., Anamaria Hanganu, and Constantin Draghici. "Trifluoroacetylation of Alcohols During NMR Study of Compounds with Bicyclo[2.2.1]heptane, Oxabicyclo[3.3.0]octane and Bicyclo[3.3.0]octane Skeleton." Revista de Chimie 72, no. 2 (May 7, 2021): 156–77. http://dx.doi.org/10.37358/rc.21.2.8428.

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TFA was added to a solution of a bicyclo[2.2.1]heptane azide-alcohol in CDCl3 to correctly characterize the compound, but during 24 h gave the trifluoro acetylated compound in quantitative yield. NMR spectra of the esterified compound helped us also to correctly attribute the NMR signals to the protons, and also confirmed the identification of the carbon atoms. The study was extended to other 14 compounds containing a primary alcohol group alone or with an ethylene ketal, a δ- or -lactone group, a primary and a secondary group, two primary and an alkene group and two primary and a secondary alcohol groups on scaffolds containing bicyclo[2.2.1]heptane, oxabicyclo[3.3.0]octane, bicyclo [2.2.1]heptane constrained with a cyclopropane ring and bicyclo[3.3.0]octane fragments. The esterification of all compounds was also quantitative in 24 to 72 h; this helped us to correct attribute the NMR signals to the protons and carbon atoms of the un-esterified compounds by comparison with those of the trifluoro acetylated compounds. A graphical presentation of 1H- and 13C-NMR spectra of a few un-esterified and esterified compounds are presented in the paper.

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Quast, Helmut, Jürgen Carlsen, Thomas Herkert, Rolf Janiak, Horst Röschert, Eva-Maria Peters, Karl Peters, and Hans Georg von Schnering. "Stereochemie der Addition von Phenylmetall-Reagenzien an Bicyclo[3.3.0]octandione und -octadiendione. — Synthese phenylsubstituierter Bicyclo[3.3.0]octadiene." Liebigs Annalen der Chemie 1992, no. 5 (May 19, 1992): 495–511. http://dx.doi.org/10.1002/jlac.199219920188.

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37

Becheanu, Armand, Thomas Bell, Sabine Laschat, Angelika Baro, Wolfgang Frey, Nelli Steinke, and Peter Fischer. "Synthesis of Pentalene Systems Employing a Sequence of Pauson-Khand Reaction, Michael Reaction, and Desilylation." Zeitschrift für Naturforschung B 61, no. 5 (May 1, 2006): 589–96. http://dx.doi.org/10.1515/znb-2006-0514.

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Abstract:

The utility of cyclopentadiene (4) in intermolecular Pauson-Khand reactions was investigated. Subsequently, a 1,4-addition of lithium organocuprates was carried out followed by desilylation. This synthetic concept allows the preparation of β -functionalized bicyclo[3.3.0]octane derivatives 1a - c in only three steps in total yields up to 53%.

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Kliegel, Wolfgang, Gottfried Lubkowitz, Steven J. Rettig, and James Trotter. "Structural studies of organoboron compounds. LIII. N,N-Diethylhydroxylamine-(O-B)1,7-dimethyl-3,5-diphenyl-2,4,6-trioxa-7-aza-1-azonia-3-bora-5- boratabicyclo[3.3.0]octane." Canadian Journal of Chemistry 70, no. 7 (July 1, 1992): 2022–26. http://dx.doi.org/10.1139/v92-254.

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Abstract:

Reaction of the condensation product of N,N′-dimethyl-N,N′-dihydroxymethanediamine and phenylboronic acid with N,N-diethylhydroxylamine gives N,N-diethylhydroxylamine(O-B)1,7-dimethyl-3,5-diphenyl-2,4,6-trioxa-7-aza-1-azonia-3-bora-5-boratabicyclo[3.3.0]octane [3-(2-ethyl-1-oxa-2-azoniabutyl)-1,7-dimethyl-3,5-diphenyl-2,4,6-trioxa-7-aza-1-azonia-3,5-diboratabicyclo[3.3.0]octane, 3] in high yield. Crystals of 3 are orthorhombic, a = 11.8132(11), b = 15.4768(11), c = 11.7325(16) Å, Z = 4, space group P212121. The structure was solved by direct methods and was refined by full-matrix least-squares procedures to R = 0.039 and Rw = 0.044 for 1729 reflections with I ≥ 2σ(I). The title compound is the second example of this recently characterized class of O-B coordinated hydroxylamine complexes, stabilized by an intramolecular [Formula: see text] hydrogen bond [Formula: see text]. Bond lengths about boron are: B—O(N) = 1.482(4)–1.526(4), B—O(B) = 1.412(4) and 1.420(4), B—N = 1.712(4), B—C = 1.591(5) and 1.602(5) Å.

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Bird, C. W., E. C. J. Coffee, and B. W. C. Schmidl. "Bicyclo [3.3.0]Octane Derivatives for Carbaprostacyclin Synthesis." Synthetic Communications 23, no. 5 (March 1, 1993): 613–20. http://dx.doi.org/10.1080/00397919308009819.

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40

Lachaise, I., K. Nohair, M. Hakiki, and J. Y. Nédélec. "A Straightforward Synthesis of [3.3.0]Bicyclic Compounds." Synthetic Communications 25, no. 22 (November 1995): 3529–36. http://dx.doi.org/10.1080/00397919508015487.

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41

Archibald, T. G., and K. Baum. "Synthesis of Polynitro-2,6-dioxabicyclo[3.3.0]octanes." Synthetic Communications 19, no. 9-10 (June 1989): 1493–98. http://dx.doi.org/10.1080/00397918908051042.

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42

Tanaka, Koichi, Tomoyuki Watanabe, and Masako Kato. "Guest-Dependent Organic Photochromism of 7-Bromo-1,4,8-Triphenyl-2,3-Benzo[3.3.0]Octa-2,4,7-Trien-6-One in the Solid State." Journal of Chemical Research 2003, no. 9 (September 2003): 535–37. http://dx.doi.org/10.3184/030823403322597207.

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Abstract:

Inclusion crystals of 7-bromo-1,4,8-triphenyl-2,3-benzo[3.3.0]octa-2,4,7-trien-6-one (1a) and its chloro-derivative (1b) showed a reversible colour change from yellow to green on exposure to UV-light, and this depends on the guest molecules present. The crystal structures of the inclusion complex were determined by X-ray analysis.

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Bartmann, Wilhelm, Gerhard Beck, Wolfram Fehlhaber, and Jiří Protiva. "Synthese von (8RS,9SR,11RS,13E,15R)-(±)-1,2,3,4-tetranor-9,11,15-trihydroxy-16,16-dimethyl-18-oxa-13-prostensäure." Collection of Czechoslovak Chemical Communications 54, no. 1 (1989): 189–95. http://dx.doi.org/10.1135/cccc19890189.

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Abstract:

Ausgehend von (1SR,5RS,6RS,7RS)-(±)-6-((1E)-4,4-Dimethyl-3-oxo-6-oxa-1-octenyl)-7-hydroxy-2-oxabicyclo[3.3.0]octan-3-on (II) wird in einer siebenstufigen Synthese (8RS,9SR,11RS,13E,15R)-(±)-1,2,3,4-Tetranor-9,11,15-trihydroxy-16,16-dimethyl-18-oxa-13-prostensäure (XII) dargestellt. Die Saure XII ist ein urinärer Hauptmetabolit des PGE2-Analog Dimoxaprost (I).

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Stachel, Hans-Dietrich, Želmíra Odlerová, and Karel Waisser. "A New Pharmacophore of Potential Antimycobacterial Activity: The Disulfide Group in the Ring of Alicyclic Compounds." Collection of Czechoslovak Chemical Communications 62, no. 3 (1997): 510–15. http://dx.doi.org/10.1135/cccc19970510.

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A series of thirty 2,3-dithiabicyclo[3.3.0]octa-4,8-diene derivatives was examined for antimycobacterial activity against Mycobacterium tuberculosis, M. kansasii, M. avium, and M. fortuitum. The structure-activity relationships were analysed by Free-Wilson method. The authors consider the disulfide moiety to be the pharmacophore of antimycobacterial activity. To verify the idea, several other monocyclic sulfides, 3,4-dihydro-1,2-dithiolane derivatives, were also evaluated.

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Butcher, Ray J., Robin Evans, and R. Gilardi. "2,4,6-Trinitro-2,4,6,8-tetraazabicyclo[3.3.0]octan-7-one." Acta Crystallographica Section E Structure Reports Online 60, no. 9 (August 21, 2004): o1543—o1545. http://dx.doi.org/10.1107/s160053680401880x.

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46

Cronan Jnr, J. M., F. R. Fronczek, and M. L. McLaughlin. "A bichromophoric difulvene from 3,7-bicyclo[3.3.0]octadione." Acta Crystallographica Section C Crystal Structure Communications 46, no. 6 (June 15, 1990): 1176–78. http://dx.doi.org/10.1107/s0108270190001445.

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47

Zharkikh, L. N., G. F. Muzychenko, V. G. Kul'nevich, V. E. Zavodnik, K. S. Pushkareva, G. V. Golovko, and A. V. Ignatenko. "Reduction of 2-oxa-3,7-diazabicyclo[3.3.0]octanes." Chemistry of Heterocyclic Compounds 28, no. 7 (July 1992): 738–41. http://dx.doi.org/10.1007/bf00474484.

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48

Hodgson, David M., and Iain D. Cameron. "Functionalized Bicyclo[3.3.0]octanes by Enantioselective Transannular Desymmetrization." Organic Letters 3, no. 3 (February 2001): 441–44. http://dx.doi.org/10.1021/ol006947n.

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49

XIANG, Y., R. F. SCHINAZI, and K. ZHAO. "ChemInform Abstract: Synthesis of (3.3.0) Bicyclic Isoxazolidinyl Nucleosides." ChemInform 27, no. 47 (August 4, 2010): no. http://dx.doi.org/10.1002/chin.199647233.

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50

Lee, Jae Wook, Ho Jung Son, Yeon Eui Jung, and Jae Ho Lee. "Synthesis of 2,7-Diazabicyclo[3.3.0]octane and 2,7-Diazabicyclo[3.3.0]oct-4-ene Derivatives via Cyclization Reaction and Julia Reaction." Synthetic Communications 26, no. 8 (April 1996): 1499–505. http://dx.doi.org/10.1080/00397919608003516.

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