Tetrahedron Letters

A convergent approach to midpacamide and dispacamide pyrrole-imidazole marine alkaloids

PM Fresneda, P Molina, MA Sanz

Index: Fresneda, Pilar M.; Molina, Pedro; Sanz, Miguel A. Tetrahedron Letters, 2001 , vol. 42, # 5 p. 851 - 854

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Citation Number: 45

Abstract

A two-step synthesis of the N-acylated α-azido-ω-aminovalerate, a common intermediate for the synthesis of midpacamide and dispacamide, is described. This intermediate undergoes cyclization through the corresponding α-ureido ester derivative to give the 3- methylhydantoin ring present in midpacamide, whereas the reaction with triphenylphosphine, tosyl isocyanate and ammonia followed by cyclization of the resulting ...