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Steroids, XLIV. Neighbouring group participation, XI. Decomposition of 2-amidomethylene-3-hydroxysteroids

✍ Scribed by Vincze, Irén ;Somlai, Csaba ;Schneider, Gyula

Book ID: 102367178
Publisher: John Wiley and Sons
Year: 1991
Tongue: English
Weight: 371 KB
Volume: 1991
Category: Article
ISSN: 0947-3440
DOI: 10.1002/jlac.1991199101181

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✦ Synopsis

Abstract

During reduction with sodium tetrahydroborate the 2‐[acetyl‐(alkyl)aminomethylene]‐3‐keto steroids 1aa, ba and 2aa – ca undergo transformation into the 2,4‐diene‐2‐aldehydes 5a and 6, respectively. These compounds are the decomposition products of the cyclic orthoester amides of the type 4a, b, formed by NAc‐6 neighbouring group participation from the 3‐hydroxy derivative A, which cannot be isolated.

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Steroids, XLV. Neighbouring Group Participation, XII. Decomposition of (Z)-16-Amidomethylene-17β-hydroxysteroids Mediated by Neighbouring Group Participation

✍ Vincze Somlai Schneider Dombi Mák, Irén Csaba Gyula György Marianna 📂 Article 📅 1992 🏛 John Wiley and Sons 🌐 English ⚖ 508 KB

## Abstract The sodium tetrahydroborate reduction of 16‐<[acetyl(alkyl)‐amino]methylene>‐17‐ketosteroids 1aa, 2aa and 2ba affords (Z)‐16‐ and (__E__)‐16‐<[acetyl(alkyl)amino]methylene>‐17β‐hydroxysteroids (Z)‐3, (__E__)‐3, (Z)‐4b, (Z)‐4a, (Z)‐5c and (__E__)‐5a. The __N__‐acetyl group of the (Z) iso