- Biosynthesis of resveratrol dimers by regioselective oxidative coupling reaction
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A wide array of natural resveratrol dimers was prepared by the regioselective oxidative coupling reaction of 3,5-di-(tert-butyl)resveratrol using several types of metal oxidants (Ag2O, Ag2CO 3, MnO2, and FeCl36H2O) in different solvent systems (benzene-acetone and dichloromethane). Subsequent debutylation of these coupling products resulted in racemic pallidol and ampelosin F. Georg Thieme Verlag Stuttgart.
- Li, Wenling,Li, Hongfu,Luo, Yaling,Yang, Yuhua,Wang, Nong
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- Total syntheses of heimiol A, hopeahainol D, and constrained analogues
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IDSI to the rescue: Use of a carefully designed cascade process empowered by the unique reagent IDSI [(Et2SI)2ClaSbCl 6] provided the entire [3.2.2] bicyclic core of both targets 1 and 2 in a single, stereocontrolled operation. Use of strain energies assisted in the completion of the natural products. Copyright
- Snyder, Scott A.,Wright, Nathan E.,Pflueger, Jason J.,Breazzano, Steven P.
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p. 8629 - 8633
(2011/11/11)
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- Total synthesis of diverse carbogenic complexity within the resveratrol class from a common building block
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Although biomimetic approaches have proven capable of converting resveratrol (1) concurrently into many of the more complex oligomers produced by plants throughout the world (such as 2-10), methods to access single members of the family have proven far more difficult to identify. Herein is described a strategy-level solution based on the use of a common building block, one distinct from Nature's starting material, that can participate in a variety of highly selective, reagent-controlled reaction cascades. These endeavors have led to the controlled synthesis of 25 natural products and analogues, molecules whose architectures encompass nearlyall the carbogenic diversity of the resveratrol family.
- Snyder, Scott A.,Breazzano, Steven P.,Ross, Audrey G.,Lin, Yunqing,Zografos, Alexandras L.
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supporting information; experimental part
p. 1753 - 1765
(2009/07/25)
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- SYNTHESIS OF RESVERATROL-BASED NATURAL PRODUCTS
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Processes for synthesizing reveratrol-based oligomers are provided. In addition, reservatrol-based oligomer compounds free of plant extract are provided.
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Page/Page column 358-359; 5/37; 25/37
(2009/04/25)
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- Total synthesis of resveratrol-based natural products: A chemoselective solution
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Despite the attention paid to resveratrol (1) owing to its potent biological activity, little effort has been devoted to studying resveratrol-based oligomers (such as 2-4). The first general synthetic approach is outlined for accessing the carbogenic diversity possessed by this family of compounds. (Chemical Equation Presented).
- Snyder, Scott A.,Zografos, Alexandros L.,Lin, Yunqing
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p. 8186 - 8191
(2008/09/18)
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- Chemical determination of the absolute structures of resveratrol dimers, ampelopsins A, B, D and F
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The absolute configurations of four stilbenedimers, (+)-ampelopsins A, (+)-ampelopsins B, (-)-ampelopsins D and (+)-ampelopsins F were respectively determined on the basis of chemical evidence.
- Takaya, Yoshiaki,Yan, Ke-Xu,Terashima, Kenji,Ito, Junko,Niwa, Masatake
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p. 7259 - 7265
(2007/10/03)
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