- 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 CONDENSED TANNINS. PART 18. STILBENES AS POTENT NUCLEOPHILES IN REGIO- AND STEREO-SPECIFIC CONDENSATIONS: NOVEL GUIBOURTINIDOL-STILBENES FROM GUIBOURTIA COLEOSPERMA
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(E)-3,3',4,5'-Tetrahydroxy- and 3',4,5'-trihydroxy-stilbenes function as strong nucleophiles in regio- and stereo-specific condensations with carbenium ions generated from 2,3-trans- and 2,3-cis-flavan-3,4,4',7-tetraols (leucoguibourtinidins) to generate
- Steynberg, Jan P.,Ferreira, Daneel,Roux, David G.
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p. 1705 - 1712
(2007/10/02)
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