Total synthesis, structural elucidation, and structure-cytotoxic activity relationship of (-)-gummiferol

Hiroyoshi Takamura, Hiroko Wada, Nan Lu, Osamu Ohno, Kiyotake Suenaga, Isao Kadota

研究成果: Article査読

14 被引用数 (Scopus)

抄録

A highly stereoselective and stereodivergent synthesis of two possible diastereomers of (-)-gummiferol was achieved, wherein the stepwise epoxidation and Cadiot-Chodkiewicz 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.

本文言語English
ページ(範囲)2443-2454
ページ数12
ジャーナルJournal of Organic Chemistry
78
6
DOI
出版ステータスPublished - 2013 3 15

ASJC Scopus subject areas

  • Organic Chemistry

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