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The chemistry of thujone. VIII . Thujone as a chiral synthon for the synthesis of optically active steroid analogues. The enol lactone route
Author(s) -
Kutney James P.,
Grice Peter,
Pascoe Keith O.,
Piotrowska Krystyna,
Rettig Steven J.,
Szykula Jerzy,
Trotter James
Publication year - 1983
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.19830660620
Subject(s) - chemistry , synthon , enol , cyclopropane , ozonolysis , enone , steroid , lactone , optically active , stereochemistry , ring (chemistry) , olefin fiber , enol ether , organic chemistry , catalysis , biochemistry , hormone
The thujone‐derived enone 1 is converted via enol lactone intermediates 4 and 5 to the optically active steroidal analogue 13 and the corresponding 19‐norsteroid analogue 14 . The structure of 13 was determined by X‐ray diffraction analysis. The acid‐catalyzed cyclopropane‐ring opening of 13 and ozonolysis of the resulting olefin provided the 16‐keto‐steroid analogue 18 .
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