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Artykuły w czasopismach na temat „Polypropionates”

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Autor: Grafiati

Data publikacji: 4 czerwca 2021

Data aktualizacji: 13 lutego 2022

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1

Blanchfield, JT, DJ Brecknell, IM Brereton, MJ Garson i DD Jones. "Caloundrin B and Funiculatin A: New Polypropionates From Siphonariid Limpets". Australian Journal of Chemistry 47, nr 12 (1994): 2255. http://dx.doi.org/10.1071/ch9942255.

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Two new polypropionates, caloundrin B (11), systematic name (1″R,2R,3″R,4R,5S,5″R,6S,-7″R,8″S,9″S,10″R)-2-(6′-ethyl-3′,5′-dimethyl-4′-oxopyran-2′-yl)-6-(5″-ethyl-7″-hydroxy-8″,9″,10″-trimethyl-2″,4″,6″-trioxatricyclo[3.3.1.13,7]dec-3″-yl)-5-hydroxy-4-methylheptan-3-one, and funiculatin A (12), systematic name (2ξ,1′S,4R,5′S,6′S)-2-(1′-ethyl-4′,6′,8′-trimethyl-2𔈀,9′-dioxabicyclo[3.3.1]nona-3′,7′-dien-3′-yl)-4,6-dimethylnon-6-en-3-one, have been isolated from Siphonaria zelandica and S. funiculata respectively. The structures of the new compounds were deduced by two-dimensional n.m.r. spectroscopy, particularly long-range 13C- 1H correlation spectroscopy (HMBC), by biosynthetic reasoning and by comparison with the known polypropionates denticulatin A (5), siphonarin B (8), muamvatin (9) and baconipyrone C (14). Information about the relative stereochemistry of the tricyclic ring system of (11) and the bicyclic ring system of (12) was deduced from coupling constant values, and by n.O.e. difference and NOESY experiments, and was confirmed by molecular modelling studies. The relative stereochemistry of the side chains and the absolute stereochemistry were inferred from biosynthetic comparison with the above known polypropionates, and by correlation of funiculatin A with denticulatin A (5) of known absolute stereochemistry. The stereochemistry at C10 of funiculatin A (position 2 of the non-6-en-3-one chain) could not be unambiguously determined. A third new polypropionate funiculatin B, epimeric with funiculatin A at C10, was isolated and partially characterized.

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2

T. Davies-Coleman, Michael, i Mary J. Garson. "Marine polypropionates". Natural Product Reports 15, nr 5 (1998): 477. http://dx.doi.org/10.1039/a815477y.

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3

Esposito, Germana, Roberta Teta, Gerardo Della Sala, Joseph Pawlik, Alfonso Mangoni i Valeria Costantino. "Isolation of Smenopyrone, a Bis-γ-Pyrone Polypropionate from the Caribbean Sponge Smenospongia aurea". Marine Drugs 16, nr 8 (17.08.2018): 285. http://dx.doi.org/10.3390/md16080285.

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The organic extract of the Caribbean sponge Smenospongia aurea has been shown to contain an array of novel chlorinated secondary metabolites derived from a mixed PKS-NRPS biogenetic route such as the smenamides. In this paper, we report the presence of a biogenetically different compound known as smenopyrone, which is a polypropionate containing two γ-pyrone rings. The structure of smenopyrone including its relative and absolute stereochemistry was determined by spectroscopic analysis (NMR, MS, ECD) and supported by a comparison with model compounds from research studies. Pyrone polypropionates are unprecedented in marine sponges but are commonly found in marine mollusks where their biosynthesis by symbiotic bacteria has been hypothesized and at least in one case demonstrated. Since pyrones have recently been recognized as bacterial signaling molecules, we speculate that smenopyrone could mediate inter-kingdom chemical communication between S. aurea and its symbiotic bacteria.

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4

Davies-Coleman, Michael T., i Mary J. Garson. "ChemInform Abstract: Marine Polypropionates". ChemInform 30, nr 10 (17.06.2010): no. http://dx.doi.org/10.1002/chin.199910319.

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5

Roke, D., M. Fañanás-Mastral i B. L. Feringa. "Iterative catalyst controlled diastereodivergent synthesis of polypropionates". Organic Chemistry Frontiers 3, nr 11 (2016): 1383–91. http://dx.doi.org/10.1039/c6qo00199h.

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6

Carmen Paul, M., Eva Zubía, Maria J. Ortega i Javier Salvá. "New polypropionates from Siphonaria pectinata". Tetrahedron 53, nr 6 (luty 1997): 2303–8. http://dx.doi.org/10.1016/s0040-4020(96)01131-3.

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7

Ward, Dale E. "The thiopyran route to polypropionates". Chemical Communications 47, nr 41 (2011): 11375. http://dx.doi.org/10.1039/c1cc13323c.

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8

Zuidema, Daniel R., i Paul B. Jones. "Photochemical Relationships in Sacoglossan Polypropionates". Journal of Natural Products 68, nr 4 (kwiecień 2005): 481–86. http://dx.doi.org/10.1021/np049607+.

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9

Gavagnin, Margherita, Aldo Spinella, Francesco Castelluccio, Guido Cimino i Arnaldo Marin. "Polypropionates from the Mediterranean Mollusk Elysia timida". Journal of Natural Products 57, nr 2 (luty 1994): 298–304. http://dx.doi.org/10.1021/np50104a017.

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10

Ward, Dale E. "ChemInform Abstract: The Thiopyran Route to Polypropionates". ChemInform 43, nr 3 (22.12.2011): no. http://dx.doi.org/10.1002/chin.201203259.

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11

Calter, Michael A., Xin Guo i Wensheng Liao. "One-Pot, Catalytic, Asymmetric Synthesis of Polypropionates". Organic Letters 3, nr 10 (maj 2001): 1499–501. http://dx.doi.org/10.1021/ol015814e.

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12

Paterson, Ian, i Jeremy P. Scott. "Polyketide library synthesis: Conformational control in extended polypropionates". Tetrahedron Letters 38, nr 42 (październik 1997): 7445–48. http://dx.doi.org/10.1016/s0040-4039(97)01752-8.

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13

Napolitano, José G., María L. Souto, José J. Fernández i Manuel Norte. "Micromelones A and B, Noncontiguous Polypropionates fromMicromelo undata". Journal of Natural Products 71, nr 2 (luty 2008): 281–84. http://dx.doi.org/10.1021/np070567u.

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14

Ward, Dale E., Vishal Jheengut i Garrison E. Beye. "Thiopyran Route to Polypropionates: An Efficient Synthesis of Serricornin". Journal of Organic Chemistry 71, nr 23 (listopad 2006): 8989–92. http://dx.doi.org/10.1021/jo061747w.

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15

Cutignano, Adele, Daniela Blihoghe, Angelo Fontana, Guido Villani, Giuliana d'Ippolito i Guido Cimino. "Fusaripyrones, novel polypropionates from the Mediterranean mollusc Haminoea fusari". Tetrahedron 63, nr 52 (grudzień 2007): 12935–39. http://dx.doi.org/10.1016/j.tet.2007.10.043.

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16

Bootwicha, Teerawut, Julian M. Feilner, Eddie L. Myers i Varinder K. Aggarwal. "Iterative assembly line synthesis of polypropionates with full stereocontrol". Nature Chemistry 9, nr 9 (10.04.2017): 896–902. http://dx.doi.org/10.1038/nchem.2757.

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17

Bromley, Candice L., Wendy L. Popplewell, Shirley C. Pinchuck, Alan N. Hodgson i Michael T. Davies-Coleman. "Polypropionates from the South African Marine Mollusk Siphonaria oculus". Journal of Natural Products 75, nr 3 (27.01.2012): 497–501. http://dx.doi.org/10.1021/np2009384.

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18

Manker, Denise C., D. John Faulkner, Thomas J. Stout i Jon Clardy. "The baconipyrones. Novel polypropionates from the pulmonate Siphonaria baconi". Journal of Organic Chemistry 54, nr 22 (październik 1989): 5371–74. http://dx.doi.org/10.1021/jo00283a036.

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19

Calter, Michael A., Xin Guo i Wensheng Liao. "ChemInform Abstract: One-Pot, Catalytic, Asymmetric Synthesis of Polypropionates." ChemInform 32, nr 35 (24.05.2010): no. http://dx.doi.org/10.1002/chin.200135054.

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20

Rovis, Tomislav, Brian Cochran, Daniel Henderson i Scott Thullen. "Rhodium-Catalyzed Desymmetrization of meso-Glutaric Anhydrides to Access Enantioenriched anti,anti-Polypropionates". Synlett 29, nr 03 (17.10.2017): 306–9. http://dx.doi.org/10.1055/s-0036-1591488.

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An expedient desymmetrization of 3,5-dimethyl-4-alkoxyglutaric anhydrides to access anti,anti-polypropionates is described. The previously unknown anhydrides are rapidly assembled from readily available precursors. A Rh(I)·t-BuPHOX catalyst system was found to provide good yield and high selectivities. With these conditions, the trisubstituted anhydrides were desymmetrized with various alkyl zinc reagents to provide synthetically useful enantioenriched anti,anti-2,4-dimethyl-3-hydroxy-δ-ketoacids. An identical catalyst system also affords access to syn,syn-stereotriads as well as a partial kinetic resolution of a chiral anhydride.

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21

Liu, Zhaoming, Hongxin Liu i Weimin Zhang. "Natural Polypropionates in 1999–2020: An Overview of Chemical and Biological Diversity". Marine Drugs 18, nr 11 (19.11.2020): 569. http://dx.doi.org/10.3390/md18110569.

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Natural polypropionates (PPs) are a large subgroup of polyketides with diverse structural features and bioactivities. Most of the PPs are discovered from marine organisms including mollusks, fungi and actinomycetes, while some of them are also isolated from terrestrial resources. An increasing number of studies about PPs have been carried out in the past two decades and an updated review is needed. In this current review, we summarize the chemical structures and biological activities of 164 natural PPs reported in 67 research papers from 1999 to 2020. The isolation, structural features and bioactivities of these PPs are discussed in detail. The chemical diversity, bioactive diversity, biodiversity and the relationship between chemical classes and the bioactivities are also concluded.

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22

Vogel, Pierre. "Total Asymmetric Synthesis of Glycomimetics and Polypropionates of Biological Interest". CHIMIA International Journal for Chemistry 62, nr 6 (25.06.2008): 519–24. http://dx.doi.org/10.2533/chimia.2008.519.

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23

Sabitha, Gowravaram, Peddabuddi Gopal i Jhillu S. Yadav. "Total synthesis of the marine polypropionates, siphonarienal, siphonarienone, and pectinatone". Tetrahedron: Asymmetry 20, nr 19 (październik 2009): 2205–10. http://dx.doi.org/10.1016/j.tetasy.2009.08.021.

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24

Beukes, Denzil R., i Michael T. Davies-Coleman. "Novel polypropionates from the South African marine mollusc Siphonaria capensis". Tetrahedron 55, nr 13 (marzec 1999): 4051–56. http://dx.doi.org/10.1016/s0040-4020(99)00093-9.

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25

PATERSON, I., i J. P. SCOTT. "ChemInform Abstract: Polyketide Library Synthesis: Conformational Control in Extended Polypropionates." ChemInform 29, nr 3 (24.06.2010): no. http://dx.doi.org/10.1002/chin.199803194.

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26

Liang, Guangxin, Ian B. Seiple i Dirk Trauner. "Stereoselective Syntheses of the Bioactive Polypropionates Aureothin,N-Acetylaureothamine, and Aureonitrile". Organic Letters 7, nr 14 (lipiec 2005): 2837–39. http://dx.doi.org/10.1021/ol050703r.

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27

Sato, Seizo, Fumie Iwata, Takako Mukai, Shoichi Yamada, Jiro Takeo, Akihisa Abe i Hiroyuki Kawahara. "Indoxamycins A−F. Cytotoxic Tricycklic Polypropionates from a Marine-Derived Actinomycete". Journal of Organic Chemistry 74, nr 15 (7.08.2009): 5502–9. http://dx.doi.org/10.1021/jo900667j.

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28

Singh, Keisham S. "Pyrone-derived Marine Natural Products: A Review on Isolation, Bio-activities and Synthesis". Current Organic Chemistry 24, nr 4 (9.05.2020): 354–401. http://dx.doi.org/10.2174/1385272824666200217101400.

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Marine natural products (MNPs) containing pyrone rings have been isolated from numerous marine organisms, and also produced by marine fungi and bacteria, particularly, actinomycetes. They constitute a versatile structure unit of bioactive natural products that exhibit various biological activities such as antibiotic, antifungal, cytotoxic, neurotoxic, phytotoxic and anti-tyrosinase. The two structure isomers of pyrone ring are γ- pyrone and α-pyrone. In terms of chemical motif, γ-pyrone is the vinologous form of α- pyrone which possesses a lactone ring. Actinomycete bacteria are responsible for the production of several α-pyrone compounds such as elijopyrones A-D, salinipyrones and violapyrones etc. to name a few. A class of pyrone metabolites, polypropionates which have fascinating carbon skeleton, is primarily produced by marine molluscs. Interestingly, some of the pyrone polytketides which are found in cone snails are actually synthesized by actinomycete bacteria. Several pyrone derivatives have been obtained from marine fungi such as Aspergillums flavus, Altenaria sp., etc. The γ-pyrone derivative namely, kojic acid obtained from Aspergillus fungus has high commercial demand and finds various applications. Kojic acid and its derivative displayed inhibition of tyrosinase activity and, it is also extensively used as a ligand in coordination chemistry. Owing to their commercial and biological significance, the synthesis of pyrone containing compounds has been given attention over the past years. Few reviews on the total synthesis of pyrone containing natural products namely, polypropionate metabolites have been reported. However, these reviews skipped other marine pyrone metabolites and also omitted discussion on isolation and detailed biological activities. This review presents a brief account of the isolation of marine metabolites containing a pyrone ring and their reported bio-activities. Further, the review covers the synthesis of marine pyrone metabolites such as cyercene-A, placidenes, onchitriol-I, onchitriol-II, crispatene, photodeoxytrichidione, (-) membrenone-C, lihualide-B, macrocyclic enol ethers and auripyrones-A & B.

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29

Danishefsky, Samuel, i Daniel F. Harvey. "A new approach to polypropionates: routes to subunits of monensin and tirandamycin". Journal of the American Chemical Society 107, nr 23 (listopad 1985): 6647–52. http://dx.doi.org/10.1021/ja00309a037.

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30

Ciavatta, M. Letizia, Enrico Trivellone, Guido Villani i Guido Cimino. "Membrenones : New polypropionates from the skin of the mediterranean mollusc Pleurobranchus membranaceus". Tetrahedron Letters 34, nr 42 (październik 1993): 6791–94. http://dx.doi.org/10.1016/s0040-4039(00)61703-3.

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31

Nuzzo, Genoveffa, Adele Cutignano, Juan Moles, Conxita Avila i Angelo Fontana. "Exiguapyrone and exiguaone, new polypropionates from the Mediterranean cephalaspidean mollusc Haminoea exigua". Tetrahedron Letters 57, nr 1 (styczeń 2016): 71–74. http://dx.doi.org/10.1016/j.tetlet.2015.11.067.

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32

Cutignano, Adele, Gonçalo Calado, Helena Gaspar, Guido Cimino i Angelo Fontana. "Polypropionates from Bulla occidentalis: chemical markers and trophic relationships in cephalaspidean molluscs". Tetrahedron Letters 52, nr 36 (wrzesień 2011): 4595–97. http://dx.doi.org/10.1016/j.tetlet.2011.06.104.

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33

Carbone, Marianna, M. Letizia Ciavatta, Jian-Rong Wang, Ilaria Cirillo, Véronique Mathieu, Robert Kiss, Ernesto Mollo, Yue-Wei Guo i Margherita Gavagnin. "Extending the Record of Bis-γ-pyrone Polypropionates from Marine Pulmonate Mollusks". Journal of Natural Products 76, nr 11 (listopad 2013): 2065–73. http://dx.doi.org/10.1021/np400483c.

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34

Ziegler, Frederick E., i Michael R. Becker. "Total synthesis of (-)-denticulatins A and B: marine polypropionates from Siphonaria denticulata". Journal of Organic Chemistry 55, nr 9 (kwiecień 1990): 2800–2805. http://dx.doi.org/10.1021/jo00296a044.

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35

Brady, Patrick B., i Hisashi Yamamoto. "Rapid and Stereochemically Flexible Synthesis of Polypropionates: Super-Silyl-Governed Aldol Cascades". Angewandte Chemie 124, nr 8 (17.01.2012): 1978–82. http://dx.doi.org/10.1002/ange.201108325.

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36

Brady, Patrick B., i Hisashi Yamamoto. "Rapid and Stereochemically Flexible Synthesis of Polypropionates: Super-Silyl-Governed Aldol Cascades". Angewandte Chemie International Edition 51, nr 8 (17.01.2012): 1942–46. http://dx.doi.org/10.1002/anie.201108325.

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37

Garson, Mary J., Jonathan M. Goodman i Ian Paterson. "A configurational model for siphonariid polypropionates derived from structural and biosynthetic considerations". Tetrahedron Letters 35, nr 37 (wrzesień 1994): 6929–32. http://dx.doi.org/10.1016/0040-4039(94)85044-5.

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38

Hosokawa, Seijiro. "Remote Asymmetric Induction Reactions and Wide Range Stereocontrol Strategy for Synthesis of Polypropionates". Journal of Synthetic Organic Chemistry, Japan 75, nr 8 (2017): 831–49. http://dx.doi.org/10.5059/yukigoseikyokaishi.75.831.

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39

Jheengut, Vishal, i Dale E. Ward. "The Thiopyran Route to Polypropionates: Enantioselective Synthesis of Membrenone B from Racemic Fragments". Journal of Organic Chemistry 72, nr 20 (wrzesień 2007): 7805–8. http://dx.doi.org/10.1021/jo701546f.

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40

Wang, Jian-Rong, Marianna Carbone, Margherita Gavagnin, Attila Mándi, Sándor Antus, Li-Gong Yao, Guido Cimino, Tibor Kurtán i Yue-Wei Guo. "Assignment of Absolute Configuration of Bis-γ-pyrone Polypropionates from Marine Pulmonate Molluscs". European Journal of Organic Chemistry 2012, nr 6 (18.01.2012): 1107–11. http://dx.doi.org/10.1002/ejoc.201101587.

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41

Exner, Claudia J., Maris Turks, Freddy Fonquerne i Pierre Vogel. "Concise Synthesis of Complicated Polypropionates through One-Pot Dissymmetrical Two-Directional Chain Elongation". Chemistry - A European Journal 17, nr 15 (8.03.2011): 4246–53. http://dx.doi.org/10.1002/chem.201003264.

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42

Pihko, Petri M., Reko Leino, Sara Källström, Anniina Erkkilä, Rainer Sjöholm i Reijo Sillanpää. "Consecutive Proline-Catalyzed Aldol Reactions and Metal-Mediated Allylations: Rapid Entries to Polypropionates". Synlett, nr 5 (2005): 0751–56. http://dx.doi.org/10.1055/s-2005-864791.

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43

Ward, Dale E., Cheng Guo, Pradip K. Sasmal, Chuk C. Man i Marcelo Sales. "Thiopyran Route to Polypropionates: Aldol Diastereoselectivity of Linear and Two-Directional Iterative Homologations". Organic Letters 2, nr 9 (maj 2000): 1325–28. http://dx.doi.org/10.1021/ol005790w.

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44

Ziegler, Frederick E., Alyssa Kneisley, John K. Thottathil i Ronald T. Wester. "3-Methyl-.gamma.-butyrolactones as templates for the synthesis of polypropionates: the basic strategy". Journal of the American Chemical Society 110, nr 16 (sierpień 1988): 5434–42. http://dx.doi.org/10.1021/ja00224a031.

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45

Ward, Dale E., Olukayode T. Akinnusi, Idralyn Q. Alarcon, Vishal Jheengut, Jianheng Shen i J. Wilson Quail. "The thiopyran route to polypropionates. Asymmetric synthesis of the building blocks by enantioselective protonation". Tetrahedron: Asymmetry 15, nr 15 (sierpień 2004): 2425–30. http://dx.doi.org/10.1016/j.tetasy.2004.06.027.

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46

Brecknell, Douglas J., Lynne A. Collett, Michael T. Davies-Coleman, Mary J. Garson i David D. Jones. "New Non-Contiguous Polypropionates from Marine Molluscs: A Comment on their Natural Product Status". Tetrahedron 56, nr 16 (kwiecień 2000): 2497–502. http://dx.doi.org/10.1016/s0040-4020(00)00095-8.

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47

Brady, Patrick B., i Hisashi Yamamoto. "ChemInform Abstract: Rapid and Stereochemically Flexible Synthesis of Polypropionates: Super-Silyl-Governed Aldol Cascades." ChemInform 43, nr 28 (14.06.2012): no. http://dx.doi.org/10.1002/chin.201228200.

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48

VARDARO, R. R., V. DI MARZO, A. MARIN i G. CIMINO. "ChemInform Abstract: α- and γ-Pyrone-Polypropionates from the Mediterranean Ascoglossan Mollusc Ercolania funerea." ChemInform 24, nr 7 (20.08.2010): no. http://dx.doi.org/10.1002/chin.199307289.

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49

Alagiri, Kaliyamoorthy, Shaoquan Lin, Naoya Kumagai i Masakatsu Shibasaki. "Iterative Direct Aldol Strategy for Polypropionates: Enantioselective Total Synthesis of (−)-Membrenone A and B". Organic Letters 16, nr 20 (26.09.2014): 5301–3. http://dx.doi.org/10.1021/ol5024932.

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50

Rychnovsky, Scott D., i Christopher J. Sinz. "Diastereoselective synthesis of polypropionates: Cationic couplings of 4-acetoxy-1,3-dioxanes with crotyl-metal reagents". Tetrahedron Letters 39, nr 38 (wrzesień 1998): 6811–14. http://dx.doi.org/10.1016/s0040-4039(98)01464-6.

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