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First Synthesis of a C ‐Homosteroid from Pregn‐4‐ene‐3,11,20‐trione
Author(s) -
Zhang Zonglei,
Wang Lizhong,
Bian Xiaoqin,
Sun Qian,
Xu Hangxian,
Wang Cunde
Publication year - 2011
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.201000132
Subject(s) - chemistry , ene reaction , aldol condensation , intramolecular force , condensation , stereochemistry , aldol reaction , medicinal chemistry , organic chemistry , catalysis , physics , thermodynamics
(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 .