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The synthesis of steroidal 16α,17α‐fused isoxazolines and isoxazolidines
Author(s) -
Culbertson T. P.,
Moersch G. W.,
Neuklis W. A.
Publication year - 1964
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570010517
Subject(s) - chemistry , nitrile , medicinal chemistry , diene , organic chemistry , natural rubber
The reaction of nitrile oxides with Δ 16 ‐steroids substituted at C‐17 by COCH 3 , OCOCH 3 , CN, NHCOCH 3 and H afforded 16α, 17α‐[3, 1‐(2‐isoxazolino)]‐steroids. From the reaction of C,N‐diphenylnitrone with pregna‐5,16‐diene‐3β‐ol‐20‐one acetate two isomeric products were isolated, 16α, 17α‐(2, 3‐diphenyl‐3,1‐isoxazolidino)‐pregn‐5‐en‐3β‐ol‐20‐one acetate and 16α, 17α ‐ (2, 3 ‐diphenyl ‐ 1, 3 ‐isoxazolidino)‐pregn‐5‐en‐3β‐01‐20‐one acetate.