- 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 337-339
(2009/04/25)
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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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- 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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- Total synthesis of the calphostins: Application of Fischer carbene complexes and thermodynamic control of atropisomers
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The total syntheses of the potent protein kinase C inhibitors calphostins A, B, C, and D as well as a variety of structural analogues are reported. An aminobenzannulation reaction of an enantiopure chromium Fischer carbene complex is utilized to prepare a pentasubstituted naphthylamine. After optimization of side-chain substituents, conversion of the naphthylamine to an o-naphthoquinone was followed by biomimetic oxidative dimerization using trifluoroacetic acid and air yielding a 1:2 P/M mixture of atropisomeric perylenequinones. Thermal equilibration to a 3:1 P:M atropisomeric ratio and separation of the perylenequinones followed by side chain desymmetrization and functionalization led to the total synthesis of enantio- and diastereomerically pure calphostin C in only twelve steps from commercially available starting materials. In addition, calphostins A, B, D, and several structural analogues were prepared to evaluate biological activities.
- Merlic,Aldrich,Albaneze-Walker,Saghatelian,Mammen
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p. 1297 - 1309
(2007/10/03)
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