Semisynthesis of Azedarachol from Pregnanetriol, a Degradative Product of Tigogenin
Dongshan Zhang
CAS Key Laboratory of Synthetic Chemistry of Natural Substances, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China
Search for more papers by this authorCorresponding Author
Yong Shi
CAS Key Laboratory of Synthetic Chemistry of Natural Substances, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China
CAS Key Laboratory of Synthetic Chemistry of Natural Substances, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, ChinaSearch for more papers by this authorCorresponding Author
Weisheng Tian
CAS Key Laboratory of Synthetic Chemistry of Natural Substances, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China
CAS Key Laboratory of Synthetic Chemistry of Natural Substances, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, ChinaSearch for more papers by this authorDongshan Zhang
CAS Key Laboratory of Synthetic Chemistry of Natural Substances, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China
Search for more papers by this authorCorresponding Author
Yong Shi
CAS Key Laboratory of Synthetic Chemistry of Natural Substances, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China
CAS Key Laboratory of Synthetic Chemistry of Natural Substances, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, ChinaSearch for more papers by this authorCorresponding Author
Weisheng Tian
CAS Key Laboratory of Synthetic Chemistry of Natural Substances, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China
CAS Key Laboratory of Synthetic Chemistry of Natural Substances, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, ChinaSearch for more papers by this authorAbstract
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.
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