Synthesis and Biological Evaluation of Fully Functionalized seco-Pancratistatin Analogues

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• 作者：James McNulty ; Jerald J. Nair ; Carly Griffin ; Siyaram Pandey
• 刊名：Journal of Natural Products
• 出版年：2008
• 出版时间：March 2008
• 年：2008
• 卷：71
• 期：3
• 页码：357 - 363
• 全文大小：222K
• 年卷期：v.71,no.3(March 2008)
• ISSN：1520-6025

文摘

The total synthesis of fully functionalized polyhydroxyamide B,C-seco-analogues of the anticancer compound pancratistatin (PST) (1) is reported. Key steps include an Evans’ MgCl₂-promoted anti-aldol reaction between a functionalized L-threose derivative and (R)-(+)-oxazolidinone to stereoselectively form the C-1/C-10b bond and a regiospecific radical-mediated oxidative fragmentation of a 1,3-benzylidene. The B,C-seco compounds 25 and 26 exhibited low activity (ED₅₀ > 30 µg/mL) for inducing apoptosis in human cancer cells.