Studies in Polyphenol Chemistry and Bioactivity. 1. Preparation of Building Blocks from (+)-Catechin. Procyanidin Formation. Synthesis of the Cancer Cell Growth …

W Tückmantel, AP Kozikowski…

文献索引：Tueckmantel, Werner; Kozikowski, Alan P.; Romanczyk Jr., Leo J. Journal of the American Chemical Society, 1999 ,  vol. 121,  # 51  p. 12073 - 12081

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被引用次数: 101

摘要

A project has been initiated to synthesize proanthocyanidin oligomers found in cocoa. Natural, readily available (+)-catechin was transformed into 5, 7, 3', 4'-tetra-O-benzyl-(-)- epicatechin (14) by (a) benzylation of the phenolic oxygens;(b) oxidation of the 3-alcohol to ketone by the Dess-Martin periodinane; and (c) reduction with lithium tri-sec- butylborohydride (l-Selectride) in the presence of LiBr. The additive diminishes the extent ...