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

ICG Vincze Somlai Schneider Dombi …

Index: Vincze, Iren; Somlai, Csaba; Schneider, Gyula; Dombi, Gyoergy; Mak, Marianna Liebigs Annalen der Chemie, 1992 , # 3 p. 187 - 192

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Citation Number: 7

Abstract

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) isomers (Z)-3,(Z)-4b, and (Z)-5c migrates to the 17β-hydroxyl in inert solvents, and the products suffer secondary transformation into unsaturated aldehydes 6 and 9a; ...