Total Synthesis, Structural Elucidation, and Structure鈥揅ytotoxic Activity Relationship of (鈭?-Gummiferol

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• 作者：Hiroyoshi Takamura ; Hiroko Wada ; Nan Lu ; Osamu Ohno ; Kiyotake Suenaga ; Isao Kadota
• 刊名：The Journal of Organic Chemistry
• 出版年：2013
• 出版时间：March 15, 2013
• 年：2013
• 卷：78
• 期：6
• 页码：2443-2454
• 全文大小：489K
• 年卷期：v.78,no.6(March 15, 2013)
• ISSN：1520-6904

文摘

A highly stereoselective and stereodivergent synthesis of two possible diastereomers of (鈭?-gummiferol was achieved, wherein the stepwise epoxidation and Cadiot鈥揅hodkiewicz reaction were utilized for the construction of the diepoxide moiety and triacetylene part, respectively. Detailed comparison of their ¹H and ¹³C NMR data and specific rotation with those of the natural product unambiguously elucidated the absolute stereostructure of gummiferol. In addition, the cytotoxic activity of the synthesized gummiferol, its stereoisomers, and its truncated analogues was evaluated, which clearly indicates that (1) the absolute configuration of the diepoxide moiety has little influence on the cytotoxic activity against human cancer cells and (2) the triacetylene unit is the crucial structural element required for exerting the cytotoxic activity.