4.4 Article

Synthesis of hemigossypol and its derivatives

期刊

TETRAHEDRON LETTERS
卷 51, 期 44, 页码 5757-5760

出版社

PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2010.08.089

关键词

Hemigossypol; Gossypol; Hemigossylic lactone

资金

  1. National Institutes of Health [HL68598]

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Hemigossypol (3), a sesquiterpene natural product, was previously isolated from Gossypium barbadense and was shown to display improved anti-furgal activity compared to gossypol (1), the disesquiterpene chiller of hemigossypol (3). Gossypol exhibits multiple biological activities. In order to study whether hemigossypol and its derivatives retain the various bioactivities of gossypol, we developed a short and convenient synthetic scheme to synthesize hemigossypol. This is the first de novo synthesis of this natural product. In addition derivatives of hemigossypol with various 2,5-alkyl substituents were synthesized. Modification of the synthetic scheme also afforded the natural product hemigossylic lactone (4) and its 2,5-substituted derivatives. (C) 2010 Elsevier Ltd. All rights reserved.

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