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Journal articles on the topic 'Polypropionates'

Author: Grafiati

Published: 4 June 2021

Last updated: 13 February 2022

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1

Blanchfield, JT, DJ Brecknell, IM Brereton, MJ Garson, and DD Jones. "Caloundrin B and Funiculatin A: New Polypropionates From Siphonariid Limpets." Australian Journal of Chemistry 47, no. 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. spectrosco

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2

T. Davies-Coleman, Michael, and Mary J. Garson. "Marine polypropionates." Natural Product Reports 15, no. 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 та Valeria Costantino. "Isolation of Smenopyrone, a Bis-γ-Pyrone Polypropionate from the Caribbean Sponge Smenospongia aurea". Marine Drugs 16, № 8 (17 серпня 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 polypropionate

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4

Davies-Coleman, Michael T., and Mary J. Garson. "ChemInform Abstract: Marine Polypropionates." ChemInform 30, no. 10 (June 17, 2010): no. http://dx.doi.org/10.1002/chin.199910319.

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5

Roke, D., M. Fañanás-Mastral, and B. L. Feringa. "Iterative catalyst controlled diastereodivergent synthesis of polypropionates." Organic Chemistry Frontiers 3, no. 11 (2016): 1383–91. http://dx.doi.org/10.1039/c6qo00199h.

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6

Carmen Paul, M., Eva Zubía, Maria J. Ortega, and Javier Salvá. "New polypropionates from Siphonaria pectinata." Tetrahedron 53, no. 6 (February 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, no. 41 (2011): 11375. http://dx.doi.org/10.1039/c1cc13323c.

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8

Zuidema, Daniel R., and Paul B. Jones. "Photochemical Relationships in Sacoglossan Polypropionates." Journal of Natural Products 68, no. 4 (April 2005): 481–86. http://dx.doi.org/10.1021/np049607+.

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9

Gavagnin, Margherita, Aldo Spinella, Francesco Castelluccio, Guido Cimino, and Arnaldo Marin. "Polypropionates from the Mediterranean Mollusk Elysia timida." Journal of Natural Products 57, no. 2 (February 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, no. 3 (December 22, 2011): no. http://dx.doi.org/10.1002/chin.201203259.

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11

Calter, Michael A., Xin Guo, and Wensheng Liao. "One-Pot, Catalytic, Asymmetric Synthesis of Polypropionates." Organic Letters 3, no. 10 (May 2001): 1499–501. http://dx.doi.org/10.1021/ol015814e.

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12

Paterson, Ian, and Jeremy P. Scott. "Polyketide library synthesis: Conformational control in extended polypropionates." Tetrahedron Letters 38, no. 42 (October 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, and Manuel Norte. "Micromelones A and B, Noncontiguous Polypropionates fromMicromelo undata." Journal of Natural Products 71, no. 2 (February 2008): 281–84. http://dx.doi.org/10.1021/np070567u.

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14

Ward, Dale E., Vishal Jheengut, and Garrison E. Beye. "Thiopyran Route to Polypropionates: An Efficient Synthesis of Serricornin." Journal of Organic Chemistry 71, no. 23 (November 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, and Guido Cimino. "Fusaripyrones, novel polypropionates from the Mediterranean mollusc Haminoea fusari." Tetrahedron 63, no. 52 (December 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, and Varinder K. Aggarwal. "Iterative assembly line synthesis of polypropionates with full stereocontrol." Nature Chemistry 9, no. 9 (April 10, 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, and Michael T. Davies-Coleman. "Polypropionates from the South African Marine Mollusk Siphonaria oculus." Journal of Natural Products 75, no. 3 (January 27, 2012): 497–501. http://dx.doi.org/10.1021/np2009384.

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18

Manker, Denise C., D. John Faulkner, Thomas J. Stout, and Jon Clardy. "The baconipyrones. Novel polypropionates from the pulmonate Siphonaria baconi." Journal of Organic Chemistry 54, no. 22 (October 1989): 5371–74. http://dx.doi.org/10.1021/jo00283a036.

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19

Calter, Michael A., Xin Guo, and Wensheng Liao. "ChemInform Abstract: One-Pot, Catalytic, Asymmetric Synthesis of Polypropionates." ChemInform 32, no. 35 (May 24, 2010): no. http://dx.doi.org/10.1002/chin.200135054.

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20

Rovis, Tomislav, Brian Cochran, Daniel Henderson, and Scott Thullen. "Rhodium-Catalyzed Desymmetrization of meso-Glutaric Anhydrides to Access Enantioenriched anti,anti-Polypropionates." Synlett 29, no. 03 (October 17, 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 kin

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21

Liu, Zhaoming, Hongxin Liu, and Weimin Zhang. "Natural Polypropionates in 1999–2020: An Overview of Chemical and Biological Diversity." Marine Drugs 18, no. 11 (November 19, 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 bio

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22

Vogel, Pierre. "Total Asymmetric Synthesis of Glycomimetics and Polypropionates of Biological Interest." CHIMIA International Journal for Chemistry 62, no. 6 (June 25, 2008): 519–24. http://dx.doi.org/10.2533/chimia.2008.519.

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23

Sabitha, Gowravaram, Peddabuddi Gopal, and Jhillu S. Yadav. "Total synthesis of the marine polypropionates, siphonarienal, siphonarienone, and pectinatone." Tetrahedron: Asymmetry 20, no. 19 (October 2009): 2205–10. http://dx.doi.org/10.1016/j.tetasy.2009.08.021.

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24

Beukes, Denzil R., and Michael T. Davies-Coleman. "Novel polypropionates from the South African marine mollusc Siphonaria capensis." Tetrahedron 55, no. 13 (March 1999): 4051–56. http://dx.doi.org/10.1016/s0040-4020(99)00093-9.

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25

PATERSON, I., and J. P. SCOTT. "ChemInform Abstract: Polyketide Library Synthesis: Conformational Control in Extended Polypropionates." ChemInform 29, no. 3 (June 24, 2010): no. http://dx.doi.org/10.1002/chin.199803194.

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26

Liang, Guangxin, Ian B. Seiple, and Dirk Trauner. "Stereoselective Syntheses of the Bioactive Polypropionates Aureothin,N-Acetylaureothamine, and Aureonitrile." Organic Letters 7, no. 14 (July 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, and Hiroyuki Kawahara. "Indoxamycins A−F. Cytotoxic Tricycklic Polypropionates from a Marine-Derived Actinomycete." Journal of Organic Chemistry 74, no. 15 (August 7, 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, no. 4 (May 9, 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 &#947;- pyrone and &#945;-pyrone. In terms of chemical motif, &#947;-pyrone is the vinologous form of &#945;- pyrone which possesses a lactone ring. Acti

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29

Danishefsky, Samuel, and Daniel F. Harvey. "A new approach to polypropionates: routes to subunits of monensin and tirandamycin." Journal of the American Chemical Society 107, no. 23 (November 1985): 6647–52. http://dx.doi.org/10.1021/ja00309a037.

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30

Ciavatta, M. Letizia, Enrico Trivellone, Guido Villani, and Guido Cimino. "Membrenones : New polypropionates from the skin of the mediterranean mollusc Pleurobranchus membranaceus." Tetrahedron Letters 34, no. 42 (October 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, and Angelo Fontana. "Exiguapyrone and exiguaone, new polypropionates from the Mediterranean cephalaspidean mollusc Haminoea exigua." Tetrahedron Letters 57, no. 1 (January 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, and Angelo Fontana. "Polypropionates from Bulla occidentalis: chemical markers and trophic relationships in cephalaspidean molluscs." Tetrahedron Letters 52, no. 36 (September 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 та Margherita Gavagnin. "Extending the Record of Bis-γ-pyrone Polypropionates from Marine Pulmonate Mollusks". Journal of Natural Products 76, № 11 (листопад 2013): 2065–73. http://dx.doi.org/10.1021/np400483c.

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34

Ziegler, Frederick E., and Michael R. Becker. "Total synthesis of (-)-denticulatins A and B: marine polypropionates from Siphonaria denticulata." Journal of Organic Chemistry 55, no. 9 (April 1990): 2800–2805. http://dx.doi.org/10.1021/jo00296a044.

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35

Brady, Patrick B., and Hisashi Yamamoto. "Rapid and Stereochemically Flexible Synthesis of Polypropionates: Super-Silyl-Governed Aldol Cascades." Angewandte Chemie 124, no. 8 (January 17, 2012): 1978–82. http://dx.doi.org/10.1002/ange.201108325.

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36

Brady, Patrick B., and Hisashi Yamamoto. "Rapid and Stereochemically Flexible Synthesis of Polypropionates: Super-Silyl-Governed Aldol Cascades." Angewandte Chemie International Edition 51, no. 8 (January 17, 2012): 1942–46. http://dx.doi.org/10.1002/anie.201108325.

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37

Garson, Mary J., Jonathan M. Goodman, and Ian Paterson. "A configurational model for siphonariid polypropionates derived from structural and biosynthetic considerations." Tetrahedron Letters 35, no. 37 (September 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, no. 8 (2017): 831–49. http://dx.doi.org/10.5059/yukigoseikyokaishi.75.831.

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39

Jheengut, Vishal, and Dale E. Ward. "The Thiopyran Route to Polypropionates: Enantioselective Synthesis of Membrenone B from Racemic Fragments." Journal of Organic Chemistry 72, no. 20 (September 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 та Yue-Wei Guo. "Assignment of Absolute Configuration of Bis-γ-pyrone Polypropionates from Marine Pulmonate Molluscs". European Journal of Organic Chemistry 2012, № 6 (18 січня 2012): 1107–11. http://dx.doi.org/10.1002/ejoc.201101587.

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41

Exner, Claudia J., Maris Turks, Freddy Fonquerne, and Pierre Vogel. "Concise Synthesis of Complicated Polypropionates through One-Pot Dissymmetrical Two-Directional Chain Elongation." Chemistry - A European Journal 17, no. 15 (March 8, 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, and Reijo Sillanpää. "Consecutive Proline-Catalyzed Aldol Reactions and Metal-Mediated Allylations: Rapid Entries to Polypropionates." Synlett, no. 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, and Marcelo Sales. "Thiopyran Route to Polypropionates: Aldol Diastereoselectivity of Linear and Two-Directional Iterative Homologations." Organic Letters 2, no. 9 (May 2000): 1325–28. http://dx.doi.org/10.1021/ol005790w.

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44

Ziegler, Frederick E., Alyssa Kneisley, John K. Thottathil, and Ronald T. Wester. "3-Methyl-.gamma.-butyrolactones as templates for the synthesis of polypropionates: the basic strategy." Journal of the American Chemical Society 110, no. 16 (August 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, and J. Wilson Quail. "The thiopyran route to polypropionates. Asymmetric synthesis of the building blocks by enantioselective protonation." Tetrahedron: Asymmetry 15, no. 15 (August 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, and David D. Jones. "New Non-Contiguous Polypropionates from Marine Molluscs: A Comment on their Natural Product Status." Tetrahedron 56, no. 16 (April 2000): 2497–502. http://dx.doi.org/10.1016/s0040-4020(00)00095-8.

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47

Brady, Patrick B., and Hisashi Yamamoto. "ChemInform Abstract: Rapid and Stereochemically Flexible Synthesis of Polypropionates: Super-Silyl-Governed Aldol Cascades." ChemInform 43, no. 28 (June 14, 2012): no. http://dx.doi.org/10.1002/chin.201228200.

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48

VARDARO, R. R., V. DI MARZO, A. MARIN та G. CIMINO. "ChemInform Abstract: α- and γ-Pyrone-Polypropionates from the Mediterranean Ascoglossan Mollusc Ercolania funerea." ChemInform 24, № 7 (20 серпня 2010): no. http://dx.doi.org/10.1002/chin.199307289.

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49

Alagiri, Kaliyamoorthy, Shaoquan Lin, Naoya Kumagai, and Masakatsu Shibasaki. "Iterative Direct Aldol Strategy for Polypropionates: Enantioselective Total Synthesis of (−)-Membrenone A and B." Organic Letters 16, no. 20 (September 26, 2014): 5301–3. http://dx.doi.org/10.1021/ol5024932.

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50

Rychnovsky, Scott D., and Christopher J. Sinz. "Diastereoselective synthesis of polypropionates: Cationic couplings of 4-acetoxy-1,3-dioxanes with crotyl-metal reagents." Tetrahedron Letters 39, no. 38 (September 1998): 6811–14. http://dx.doi.org/10.1016/s0040-4039(98)01464-6.

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