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First Synthesis of a C-Homosteroid from Pregn-4-ene-3,11,20-trione

✍ Scribed by Zonglei Zhang; Lizhong Wang; Xiaoqin Bian; Qian Sun; Hangxian Xu; Cunde Wang

Publisher
John Wiley and Sons
Year
2011
Tongue
German
Weight
177 KB
Volume
94
Category
Article
ISSN
0018-019X

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✦ Synopsis

Abstract

(3__α__,5__α__)‐3‐Hydroxy‐C‐homopregnane‐11,20‐dione (3) was prepared in eleven steps from the commercially available pregn‐4‐ene‐3,11,20‐trione (4) via the 11‐oxo‐13‐formyl‐12,13‐secopregnane intermediate 11 (Scheme 2). Subjection of this secopregnane to an intramolecular aldol condensation afforded the α,β‐unsaturated key intermediate C‐homopregn‐12‐en‐11‐one 12.

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