Premium
A Scalable Synthesis of 6,19‐Dihydroxyandrostenedione
Author(s) -
Yan Yubo,
Li Ting,
Liu Tao,
Dou Qingyu,
Ding Kai,
Tian Weisheng
Publication year - 2013
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.201201023
Subject(s) - chemistry , isomerization , yield (engineering) , stereospecificity , allylic rearrangement , combinatorial chemistry , key (lock) , sequence (biology) , scalability , organic chemistry , catalysis , database , biochemistry , computer science , materials science , metallurgy , computer security
Starting from the commercially available 19‐hydroxyandrostenedione, a practical protocol for the preparation of 6,19‐dihydroxyandrostenedione is reported. This compound is a key intermediate for the synthesis of cyclocitrinols. With the stereospecific epoxidation and following isomerization to allylic alcohol as key steps, a six‐step procedure provided desired product in high yield. The sequence is easy to scale‐up without the need of laborious chromatography.