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

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

Research output: Contribution to journalArticle

13 Citations (Scopus)

Abstract

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.

Original languageEnglish
Pages (from-to)2443-2454
Number of pages12
JournalJournal of Organic Chemistry
Volume78
Issue number6
DOIs
Publication statusPublished - Mar 15 2013

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Stereoisomerism
Epoxidation
Biological Products
Cells
Nuclear magnetic resonance
gummiferol

ASJC Scopus subject areas

  • Organic Chemistry

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Total synthesis, structural elucidation, and structure-cytotoxic activity relationship of (-)-gummiferol. / Takamura, Hiroyoshi; Wada, Hiroko; Lu, Nan; Ohno, Osamu; Suenaga, Kiyotake; Kadota, Isao.

In: Journal of Organic Chemistry, Vol. 78, No. 6, 15.03.2013, p. 2443-2454.

Research output: Contribution to journalArticle

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