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Regioselective Olefination of Cross-Conjugated 3-Thioxosteroids by [3+2] Cycloaddition

✍ Scribed by Fiedler, Beate ;Weiß, Dieter ;Beckert, Rainer

Publisher: John Wiley and Sons
Year: 1997
Tongue: English
Weight: 371 KB
Volume: 1997
Category: Article
ISSN: 0947-3440
DOI: 10.1002/jlac.199719970324

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✦ Synopsis

Abstract

Reaction of 3‐thioxoandrosta‐1,4‐dien‐17‐one (1) with the diazo compounds 2a–i affords 4′‐substituted spiro[17‐oxoandrosta‐1,4‐diene‐3,2′‐[1,3,4]thiadiazolines], which undergo a two‐step ring contraction with extrusion of nitrogen and sulfur, leading to the substituted 3‐methylen‐ and 3‐propylidenandrosta‐1,4‐dien‐17‐ones 3a–i in good yields.

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