Convergent total synthesis of (.+-.)-colchicine and (.+-.)-desacetamidoisocolchicine

DA Evans, SP Tanis, DJ Hart

Index: Evans; Tanis; Hart Journal of the American Chemical Society, 1981 , vol. 103, # 19 p. 5813 - 5821

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Citation Number: 85

Abstract

Abstract: Total syntheses of (&)-desacetamidoisoolchicine (2b) and (&)-colchicine (la) have been achieved. Key features of the synthetic sequence are the facile incorporation of a tropolone dication equivalent via ketone 6 and introduction of the 7-acetamido group. Some of the mechanistic details of the conversion of alcohol 7 to dihydrotropolone 8 and alcohols 14a, b to ester 19 are discussed.