First Synthesis of a  C ‐Homosteroid from Pregn‐4‐ene‐3,11,20‐trione | Zendy

Zhang Zonglei | Zendy; Wang Lizhong | Zendy; Bian Xiaoqin | Zendy; Sun Qian | Zendy; Xu Hangxian | Zendy; Wang Cunde | Zendy

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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 .

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