Cationic cyclization of ketene dithioacetals. A general synthesis of pyrrolizidine, indolizidine, and quinolizidine alkaloid ring systems
AR Chamberlin, D Nguyen Hoa…
Index: Chamberlin, A.Richard; Nguyen, Hoa D.; Chung, John Y.L. Journal of Organic Chemistry, 1984 , vol. 49, # 10 p. 1682 - 1688
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Citation Number: 71
Abstract
Cyclizations of ketene dithioacetals have been applied to the synthesis of pyrrolizidine, indolizidine, and quinolizidine alkaloid ring systems. This new cationic cyclization terminator allows the efficient formation of 5-, 6-, and 7-membered heterocyclic rings, as illustrated by the preparation of 10a-e. Several of these products, available in three steps, have been converted into the known alkaloids (&)-supinidine,(A)-trachelanthamidine,
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