268550-11-4Relevant articles and documents
SYNTHESIS OF RESVERATROL-BASED NATURAL PRODUCTS
-
Page/Page column 337-339, (2009/04/25)
Processes for synthesizing reveratrol-based oligomers are provided. In addition, reservatrol-based oligomer compounds free of plant extract are provided.
Total synthesis of diverse carbogenic complexity within the resveratrol class from a common building block
Snyder, Scott A.,Breazzano, Steven P.,Ross, Audrey G.,Lin, Yunqing,Zografos, Alexandras L.
supporting information; experimental part, p. 1753 - 1765 (2009/07/25)
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.
Total synthesis of resveratrol-based natural products: A chemoselective solution
Snyder, Scott A.,Zografos, Alexandros L.,Lin, Yunqing
, p. 8186 - 8191 (2008/09/18)
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).
Total synthesis of the calphostins: Application of Fischer carbene complexes and thermodynamic control of atropisomers
Merlic,Aldrich,Albaneze-Walker,Saghatelian,Mammen
, p. 1297 - 1309 (2007/10/03)
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.
