Tetrahedron

The application of the sulphide contraction to the synthesis of some simple pyrrolidine alkaloids

R Ghirlando, AS Howard, RB Katz, JP Michael

Index: Ghirlando, Rodolfo; Howard, Arthur S.; Katz, Ruth B.; Michael, Joseph P. Tetrahedron, 1984 , vol. 40, # 15 p. 2879 - 2884

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Citation Number: 24

Abstract

The alkaloids (±)-hygrine,(±)-dehydrodarlinine,(±)-dehydrodarlingianine, and (±)-N- methylruspolinone have been synthesised by selective reduction of vinylogous amides formed by sulphide contraction of the salts prepared by reaction of N-methyl-2- thiopyrrolidone with the appropriate bromomethyl ketones.