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Journal articles on the topic 'Spiroketals'

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Published: 4 June 2021

Last updated: 10 February 2022

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1

Čikoš, Ana, Irena Ćaleta, Dinko Žiher, Mark B. Vine, Ivaylo J. Elenkov, Marko Dukši, Dubravka Gembarovski, et al. "Structure and conformational analysis of spiroketals from 6-O-methyl-9(E)-hydroxyiminoerythronolide A." Beilstein Journal of Organic Chemistry 11 (August 19, 2015): 1447–57. http://dx.doi.org/10.3762/bjoc.11.157.

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Three novel spiroketals were prepared by a one-pot transformation of 6-O-methyl-9(E)-hydroxyiminoerythronolide A. We present the formation of a [4.5]spiroketal moiety within the macrolide lactone ring, but also the unexpected formation of a 10-C=11-C double bond and spontaneous change of stereochemistry at position 8-C. As a result, a thermodynamically stable structure was obtained. The structures of two new diastereomeric, unsaturated spiroketals, their configurations and conformations, were determined by means of NMR spectroscopy and molecular modelling. The reaction kinetics and mechanistic aspects of this transformation are discussed. These rearrangements provide a facile synthesis of novel macrolide scaffolds.

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2

Messerle, Barbara A., and Khuong Q. Vuong. "Synthesis of spiroketals by iridium-catalyzed double hydroalkoxylation." Pure and Applied Chemistry 78, no. 2 (January 1, 2006): 385–90. http://dx.doi.org/10.1351/pac200678020385.

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A highly efficient approach to the synthesis of spiroketals involves the double cyclization of alkynyl diols using transition-metal catalysts. The iridium complex [Ir(PyP)(CO)2]BPh4 where PyP = 1-[(2-diphenylphosphino)ethyl]pyrazole is an effective catalyst for promoting the formation of spiroketals via this double hydroalkoxylation reaction. The complex promotes the formation of a series of spiroketal products from alkynyl diol starting materials such as 3-ethynylpentane-1,5-diol and 2-(4-hydroxybut-1-ynyl)benzyl alcohol. Stereoselective cyclization occurs for 3-ethynylpentane-1,5-diol, 3-ethynylhexane-1,6-diol. The cycloadditions occur in all but one case with quantitative conversion in under 24 h at 120 °C.

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3

Brimble, Margaret A., and Seng H. Chan. "Synthesis of 7-Methoxy-3′,4′,5′,6′-tetrahydrospiro-[isobenzofuran-1(3H),2′-pyran]-3-one and 5,7-Dimethoxy-3′,4′,5′,6′-tetrahydrospiro[isobenzofuran-1(3H),2′-pyran]-3-one." Australian Journal of Chemistry 51, no. 3 (1998): 235. http://dx.doi.org/10.1071/c97193.

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The synthesis of novel aryl spiroketals, which contain a similar substitution pattern to that present in the antifungal agents the papulacandins, is described. Thus, spiroketal (7) was obtained from acid-catalysed cyclization of the keto alcohol (13), and spiroketal (8) was obtained from acid-catalysed cyclization of keto alcohols (12) and (19). Keto alcohols (12), (13) and (19) in turn were prepared by ortho-directed lithiation of amides (10), (11) and oxazoline (17) respectively, followed by reaction with δ-valerolactone. Substitution of the aromatic ring occurred at the sterically hindered position ortho to both the methoxy and ortho-directing metalation group. In an alternative approach to the synthesis of the desired spiroketals, two palladium(0)-catalysed coupling strategies were examined. The Stille coupling between the aryl stannane (24) and iodoglucal (25) resulted in a low yield of the aryl C-glycoside (21). Likewise, a low yield for the same coupled product (21) was achieved by a Suzuki coupling between the arylboronic acid (26) and iodoglucal (25).

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4

Tlais, Sami F., and Gregory B. Dudley. "On the proposed structures and stereocontrolled synthesis of the cephalosporolides." Beilstein Journal of Organic Chemistry 8 (August 14, 2012): 1287–92. http://dx.doi.org/10.3762/bjoc.8.146.

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The synthesis of four candidate stereoisomers of cephalosporolide H is described, made possible by a zinc-chelation strategy for controlling the stereochemistry of oxygenated 5,5-spiroketals. The same strategy likewise enables the first stereocontrolled synthesis of cephalosporolide E, which is typically isolated and prepared admixed with its spiroketal epimer, cephalosporolide F.

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5

Green, Jason C., G. Leslie Burnett, and Thomas R. R. Pettus. "New strategies for natural products containing chroman spiroketals." Pure and Applied Chemistry 84, no. 7 (May 2, 2012): 1621–31. http://dx.doi.org/10.1351/pac-con-11-10-34.

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Two cycloaddition strategies are described that lead to various chroman spiroketals from assorted exocyclic enol ethers. Unlike conventional thermodynamic ketalization strategies, the stereochemical outcome for this approach is determined by a kinetic cycloaddition reaction. Thus, the stereochemical outcome reflects the olefin geometry of the starting materials along with the orientation of the associated transition state. However, the initial kinetic product can also be equilibrated by acid catalysis and reconstituted into a thermodynamic stereochemical arrangement. Thus, these strategies uniquely enable synthetic access to either the thermodynamic or kinetic conformation of the spiroketal stereocenter itself. Applications of these strategies in the syntheses of berkelic acid, β-rubromycin, and paecilospirone are presented along with the use of a chroman spiroketal for the construction of heliespirones A and C.

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6

Lee, Seongmin, and Philip L. Fuchs. "In situ nitrosonium ion generation — α-Oximinylation of enol ethers from steroidal spiroketals: Introduction of C23 (R)-OH in cephalostatin intermediates." Canadian Journal of Chemistry 84, no. 10 (October 1, 2006): 1442–47. http://dx.doi.org/10.1139/v06-113.

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Nitrosonium ion generated in situ from the reaction of t-BuNO2 and BF3·Et2 is an effective oximinylating agent for enol ethers derived from steroidal spiroketals. The scope and limitations of this method has been studied. The difficult reduction of C23 ketone to C23 (R)-alcohol has now been selectively achieved via L-Selectride® reduction. Application to cephalostatin intermediates is discussed.Key words: oximinylation, nitrosonium ion, steroid spiroketal, cephalostatins.

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7

Tlais, Sami F., and Gregory B. Dudley. "A gold-catalyzed alkyne-diol cycloisomerization for the synthesis of oxygenated 5,5-spiroketals." Beilstein Journal of Organic Chemistry 7 (May 4, 2011): 570–77. http://dx.doi.org/10.3762/bjoc.7.66.

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A highly efficient synthesis of oxygenated 5,5-spiroketals was performed towards the synthesis of the cephalosporolides. Gold(I) chloride in methanol induced the cycloisomerization of a protected alkyne triol with concomitant deprotection to give a strategically hydroxylated 5,5-spiroketal, despite the potential for regiochemical complications and elimination to furan. Other late transition metal Lewis acids were less effective. The use of methanol as solvent helped suppress the formation of the undesired furan by-product. This study provides yet another example of the advantages of gold catalysis in the activation of alkyne π-systems.

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8

Perron, Francoise, and Kim F. Albizati. "Chemistry of spiroketals." Chemical Reviews 89, no. 7 (November 1989): 1617–61. http://dx.doi.org/10.1021/cr00097a015.

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9

Balachandran, Raghavan, Tamara D. Hopkins, Catherine A. Thomas, Peter Wipf, and Billy W. Day. "Tubulin-Perturbing Naphthoquinone Spiroketals." Chemical Biology & Drug Design 71, no. 2 (February 2008): 117–24. http://dx.doi.org/10.1111/j.1747-0285.2007.00616.x.

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10

Ardes-Guisot, Nicolas, Bani Ouled-Lahoucine, Isabelle Canet, and Marie-Eve Sinibaldi. "A straightforward route to spiroketals." Tetrahedron Letters 48, no. 48 (November 2007): 8511–13. http://dx.doi.org/10.1016/j.tetlet.2007.09.151.

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11

Brimble, Margaret A., Michael K. Edmonds, and Geoffrey M. Williams. "Allylic oxidation of unsaturated spiroketals." Tetrahedron Letters 31, no. 51 (January 1990): 7509–12. http://dx.doi.org/10.1016/s0040-4039(00)88531-7.

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12

Chen, Xinzheng, and Sasa Wang. "Photoinduced Synthesis of Benzannulated Spiroketals." Synlett 26, no. 14 (June 25, 2015): 2042–46. http://dx.doi.org/10.1055/s-0034-1381038.

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13

Anderson, E. A., and B. Gockel. "ChemInform Abstract: Spiroketals (Update 2010)." ChemInform 42, no. 38 (August 25, 2011): no. http://dx.doi.org/10.1002/chin.201138216.

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14

Brimble, Margaret A., David L. Officer, and Geoffrey M. Williams. "A facile synthesis of spiroketals." Tetrahedron Letters 29, no. 29 (January 1988): 3609–12. http://dx.doi.org/10.1016/0040-4039(88)85307-3.

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15

Gillard, Rachel M., and Margaret A. Brimble. "Benzannulated spiroketal natural products: isolation, biological activity, biosynthesis, and total synthesis." Organic & Biomolecular Chemistry 17, no. 36 (2019): 8272–307. http://dx.doi.org/10.1039/c9ob01598a.

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16

Quach, Rachelle, Daniel F. Chorley, and Margaret A. Brimble. "Recent developments in transition metal-catalysed spiroketalisation." Org. Biomol. Chem. 12, no. 38 (2014): 7423–32. http://dx.doi.org/10.1039/c4ob01325e.

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17

Mayorquín-Torres, Martha C., Juan Carlos González-Orozco, Marcos Flores-Álamo, Ignacio Camacho-Arroyo, and Martín A. Iglesias-Arteaga. "Palladium catalyzed synthesis of benzannulated steroid spiroketals." Organic & Biomolecular Chemistry 18, no. 4 (2020): 725–37. http://dx.doi.org/10.1039/c9ob02255d.

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Nine cytotoxic [5/7] and [6/6] benzannulated steroid spiroketals were synthesized by palladium catalyzed spiroketalization of 5α and 5β-alkynediols derived from testosterone, diosgenin and cholesterol.

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18

Zhang, Fu-Min, Shu-Yu Zhang, and Yong-Qiang Tu. "Recent progress in the isolation, bioactivity, biosynthesis, and total synthesis of natural spiroketals." Natural Product Reports 35, no. 1 (2018): 75–104. http://dx.doi.org/10.1039/c7np00043j.

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19

Teng, Qi, Jialin Qi, Ling Zhou, Zhenghu Xu, and Chen-Ho Tung. "Synthesis of benzannulated spiroketals with gold-catalyzed cycloisomerization/spiroketalization cascade." Organic Chemistry Frontiers 5, no. 6 (2018): 990–93. http://dx.doi.org/10.1039/c7qo01005b.

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20

Raju, B., and Anil Saikia. "Asymmetric Synthesis of Naturally Occuring Spiroketals." Molecules 13, no. 8 (August 28, 2008): 1942–2038. http://dx.doi.org/10.3390/molecules13081942.

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21

Zemribo, Ronald, and Keith T. Mead. "A novel route to monoanomeric spiroketals." Tetrahedron Letters 39, no. 23 (June 1998): 3891–94. http://dx.doi.org/10.1016/s0040-4039(98)00685-6.

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22

Bray, Christopher. "An Approach to Benzannelated [5,6]-Spiroketals." Synlett 2008, no. 16 (September 12, 2008): 2500–2502. http://dx.doi.org/10.1055/s-2008-1078057.

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23

Crimmins, Michael T., and Rosemary O'Mahony. "Synthesis of spiroketals: a general approach." Journal of Organic Chemistry 55, no. 23 (November 1990): 5894–900. http://dx.doi.org/10.1021/jo00310a023.

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24

Sommer, Stefan, Marc Kühn, and Herbert Waldmann. "Solid-Phase Synthesis of [5.5]-Spiroketals." Advanced Synthesis & Catalysis 350, no. 11-12 (August 4, 2008): 1736–50. http://dx.doi.org/10.1002/adsc.200800154.

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25

Pale, P., and J. Chuche. "A two step synthesis of spiroketals." Tetrahedron Letters 29, no. 24 (January 1988): 2947–50. http://dx.doi.org/10.1016/0040-4039(88)85054-8.

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26

Brimble, Margaret A., Michael R. Nairn, and Yinqiu Wu. "Highly stereoselective syn-hydroxylation of spiroketals." Tetrahedron Letters 32, no. 32 (August 1991): 4049–50. http://dx.doi.org/10.1016/0040-4039(91)80625-g.

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27

Wood, James M., Daniel P. Furkert, and Margaret A. Brimble. "Synthesis of the 2-formylpyrrole spiroketal pollenopyrroside A and structural elucidation of xylapyrroside A, shensongine A and capparisine B." Organic & Biomolecular Chemistry 14, no. 32 (2016): 7659–64. http://dx.doi.org/10.1039/c6ob01361a.

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A convergent synthesis enabled structural elucidation of the 2-formyl pyrrole spiroketals pollenopyrroside A and shensongine A/xylapyrroside A. The key step involves a Maillard-type condensation to furnish the 2-formylpyrrole ring system.

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28

Nicolas, Lionel, Alexey N. Butkevich, Amandine Guérinot, Andrei Corbu, Sébastien Reymond, and Janine Cossy. "Synthesis of complex oxygenated heterocycles." Pure and Applied Chemistry 85, no. 6 (March 27, 2013): 1203–13. http://dx.doi.org/10.1351/pac-con-12-09-15.

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Versatile and chemoselective preparation of substituted oxygenated heterocycles is described. Highly diastereoselective metal-catalyzed syntheses of trans-2,6- and cis-2,6-disubstituted tetrahydropyrans (THPs) are presented, along with an easy one-pot access to various ring size benzoannulated spiroketals.

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29

LaCour, Thomas G., and P. L. Fuchs. "Concurrent ring opening and halogenation of spiroketals." Tetrahedron Letters 40, no. 25 (June 1999): 4655–58. http://dx.doi.org/10.1016/s0040-4039(99)00827-8.

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30

Oikawa, Hideaki, Masato Oikawa, Akitami Ichihara, Kimiko Kobayashi, and Masakazu Uramoto. "Highly regio- and stereoselective reductions of spiroketals." Tetrahedron Letters 34, no. 33 (August 1993): 5303–6. http://dx.doi.org/10.1016/s0040-4039(00)73980-3.

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31

Dalla, V., and P. Pale. "Diastereoselective synthesis of spiroketals via radical cyclization." Tetrahedron Letters 33, no. 51 (December 1992): 7857–60. http://dx.doi.org/10.1016/s0040-4039(00)74762-9.

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32

Brown, Christopher D. S., Nigel S. Simpkins, and Keith Clinch. "A route to spiroketals using radical translocation." Tetrahedron Letters 34, no. 1 (January 1993): 131–32. http://dx.doi.org/10.1016/s0040-4039(00)60075-8.

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33

Cahill, Shane, and Matthew O’Brien. "Furanyl spiroketals: thermodynamic control of remote asymmetry." Tetrahedron Letters 47, no. 22 (May 2006): 3665–68. http://dx.doi.org/10.1016/j.tetlet.2006.03.135.

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34

Gai, Sinan, Nigel T. Lucas, and Bill C. Hawkins. "Benzannulated 6,5-Spiroketals from Donor–Acceptor Cyclopropanes." Organic Letters 21, no. 8 (March 29, 2019): 2872–75. http://dx.doi.org/10.1021/acs.orglett.9b00878.

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35

Waller, David L., Corey R. J. Stephenson, and Peter Wipf. "Spiroketals via oxidative rearrangement of enol ethers." Org. Biomol. Chem. 5, no. 1 (2007): 58–60. http://dx.doi.org/10.1039/b612992g.

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36

Rizzacasa, Mark A., and Annett Pollex. "The hetero-Diels–Alder approach to spiroketals." Organic & Biomolecular Chemistry 7, no. 6 (2009): 1053. http://dx.doi.org/10.1039/b819966n.

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37

Lindsey, Christopher C., Kun Liang Wu, and Thomas R. R. Pettus. "Synthesis of Electron Deficient 5,6-Aryloxy Spiroketals." Organic Letters 8, no. 11 (May 2006): 2365–67. http://dx.doi.org/10.1021/ol0606886.

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38

Yoneda, Naoki, Yukihiro Fukata, Keisuke Asano, and Seijiro Matsubara. "Asymmetric Synthesis of Spiroketals with Aminothiourea Catalysts." Angewandte Chemie 127, no. 51 (October 29, 2015): 15717–20. http://dx.doi.org/10.1002/ange.201508405.

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39

Yoneda, Naoki, Yukihiro Fukata, Keisuke Asano, and Seijiro Matsubara. "Asymmetric Synthesis of Spiroketals with Aminothiourea Catalysts." Angewandte Chemie International Edition 54, no. 51 (October 29, 2015): 15497–500. http://dx.doi.org/10.1002/anie.201508405.

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40

Wilson, Zoe E., Jonathan G. Hubert, and Margaret A. Brimble. "A Flexible Approach to 6,5-Benzannulated Spiroketals." European Journal of Organic Chemistry 2011, no. 20-21 (May 18, 2011): 3938–45. http://dx.doi.org/10.1002/ejoc.201100345.

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41

BRIMBLE, M. A., M. K. EDMONDS, and G. M. WILLIAMS. "ChemInform Abstract: Allylic Oxidation of Unsaturated Spiroketals." ChemInform 23, no. 14 (August 22, 2010): no. http://dx.doi.org/10.1002/chin.199214111.

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42

Barun, Okram, Stefan Sommer, and Herbert Waldmann. "Asymmetric Solid-Phase Synthesis of 6,6-Spiroketals." Angewandte Chemie International Edition 43, no. 24 (June 14, 2004): 3195–99. http://dx.doi.org/10.1002/anie.200353609.

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43

Lawson, Elvie N., William Kitching, Colin H. L. Kennard, and Karl A. Byriel. ".alpha.-Bromo spiroketals: stereochemistry and elimination reactions." Journal of Organic Chemistry 58, no. 9 (April 1993): 2501–8. http://dx.doi.org/10.1021/jo00061a025.

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44

Brimble, Margaret A. "Synthesis of Spiroketals Related to Griseusin A." Molecules 1, no. 1 (March 29, 1996): 3–14. http://dx.doi.org/10.1007/s007830050002.

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45

Tomas, Loic, Benjamin Bourdon, Jean Claude Caille, David Gueyrard, and Peter G. Goekjian. "A Concise and Efficient Synthesis of Spiroketals - Application to the Synthesis of SPIKET-P and a Spiroketal fromBactroceraSpecies." European Journal of Organic Chemistry 2013, no. 5 (January 10, 2013): 915–20. http://dx.doi.org/10.1002/ejoc.201201199.

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46

Commandeur, Malgorzata, Claude Commandeur, and Janine Cossy. "Spiroketals: Toward the synthesis of 39-oxobistramide K." Pure and Applied Chemistry 84, no. 7 (February 29, 2012): 1567–74. http://dx.doi.org/10.1351/pac-con-11-09-06.

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An advanced spiroketal intermediate toward the synthesis of 39-oxobistramide K was prepared, fragment C14–C40. This fragment was obtained in 19 steps with an overall yield of 6.2 % using a FeCl3-catalyzed spiroketalization as the key step.

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47

Iwata, Chuzo, Kohji Hattori, Masahiro Fujita, Shuji Uchida, and Takeshi Imanishi. "Stereoselective Synthetic Studies on Biologically Active Natural Spiroketals." HETEROCYCLES 23, no. 1 (1985): 229. http://dx.doi.org/10.3987/r-1985-01-0229.

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48

Seward, Eileen M., Emma Carlson, Timothy Harrison, Karen E. Haworth, Richard Herbert, Fintan J. Kelleher, Marc M. Kurtz, et al. "Spirocyclic NK1 antagonists I: [4.5] and [5.5]-Spiroketals." Bioorganic & Medicinal Chemistry Letters 12, no. 18 (September 2002): 2515–18. http://dx.doi.org/10.1016/s0960-894x(02)00506-1.

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49

van Hooft, Peter A. V., Farid El Oualid, Herman S. Overkleeft, Gijsbert A. van der Marel, Jacques H. van Boom, and Michiel A. Leeuwenburgh. "Synthesis and elaboration of functionalised carbohydrate-derived spiroketals." Organic & Biomolecular Chemistry 2, no. 9 (2004): 1395. http://dx.doi.org/10.1039/b401699h.

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50

Winkler, Jeffrey D., and Peter J. Mikochik. "Synthesis of Cyclic Hemiketals and Spiroketals from Dioxanorbornanes." Organic Letters 6, no. 21 (October 2004): 3735–37. http://dx.doi.org/10.1021/ol048578r.

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