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Semisynthesis of Azedarachol from Pregnanetriol, a Degradative Product of Tigogenin
Author(s) -
Zhang Dongshan,
Shi Yong,
Tian Weisheng
Publication year - 2015
Publication title -
chinese journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.28
H-Index - 41
eISSN - 1614-7065
pISSN - 1001-604X
DOI - 10.1002/cjoc.201500231
Subject(s) - semisynthesis , chemistry , natural product , organic chemistry
Abstract We report the first semisynthesis of the natural insect antifeedant azedarachol. The synthesis features the employment of pregnanetriol, a degradative product of the resource natural product tigogenin, as the starting material, the symbiotic reaction involving the mutually‐promoting elimination of toluene‐sulfonate and deprotection of acetonide, and the controllable reactions between the C16‐OH and the C20‐OH in pregnane‐16,20‐diols.