Total synthesis of lycopodium alkaloids:(.+-.)-lycopodine,(.+-.)-lycodine, and (.+-.)-lycodoline

CH Heathcock, EF Kleinman…

Index: Heathcock, Clayton H.; Kleinman, Edward F.; Binkley, Edward S. Journal of the American Chemical Society, 1982 , vol. 104, # 4 p. 1054 - 1068

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Citation Number: 103

Abstract

Abstract: Intramolecular Mannich condensation is shown to be a powerful method for the synthesis of lycopodium alkaloids (eq 2). Two syntheses of (A)-lycopodine (1) have been developed. In the first (Scheme 11), compound 1 is produced in 13 steps from 5-methyl-l, 3- cyclohexanedione (16.6% overall yield). In this synthesis, rings A and B are formed in the Mannich cyclization, and ring D is closed by aldol condensation. The alternative ...