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The chemistry of thujone. IX. Thujone as a chiral synthon for the synthesis of optically active steroid analogues. The vinylpicoline route

✍ Scribed by James P. Kutney; Peter Grice; Krystyna Piotrowska; Steven J. Rettig; Jerzy Szykula; James Trotter; Loc Van Chu

Publisher
John Wiley and Sons
Year
1983
Tongue
German
Weight
432 KB
Volume
66
Category
Article
ISSN
0018-019X

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✦ Synopsis

Abstract

The thujone‐derived enone 1, upon base‐catalyzed reaction with 2‐methyl‐6‐vinylpyridine is converted to the pyridine analogue 5 (Scheme 1). Catalytic reduction of the latter to 6 generates two new centers of chirality which eventually become C(8) and C(14) in the ultimate synthetic steroid analogue 12. An X‐ray analysis of 6 establishes the structure and absolute configuration so as to determine its suitability in subsequent synthetic studies. The acetal derivative 7, via Birch reduction, hydrolysis, and internal aldol cyclization, is converted into the cyclohexenone analogue 10 (Scheme 2). This ‘one‐pot’ process affords an efficient conversion of the pyridine ring into a cyclohexenone system required for A‐ring construction of the steroid skeleton. Finally, conversion of 10, via the unsaturated diketone 11, provides the chiral steroid analogue 12.

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## Abstract ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable v