Stereoselective total syntheses of the antitumor antibiotics (+)-actinobolin and (-)-bactobolin from a common bridged lactone intermediate

RS Garigipati, DM Tschaen…

Index: Garigipati; Tschaen; Weinreb Journal of the American Chemical Society, 1990 ,  vol. 112,  # 9  p. 3475 - 3482

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Citation Number: 35

Abstract

Abstract: Efficient, highly stereoselective approaches have been developed to (+)- actinobolin (1) and (-)-bactobolin (3) from bridged a-keto lactone 11, which can be readily prepared via intramolecular SnCI4 catalyzed ene reaction of cyclohexenol glyoxylate (5). A novel method has been developed for direct, stereoselective reductive sulfonamidation of 11 to simultaneously introduce a protected C-4 amino group of the natural products and ...