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

✍ Scribed by Pilar M Fresneda; Pedro Molina; Miguel A Sanz

Book ID: 104211615
Publisher: Elsevier Science
Year: 2001
Tongue: French
Weight: 86 KB
Volume: 42
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(00)02120-1

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✦ Synopsis

A two-step synthesis of the N-acylated a-azido-v-aminovalerate, a common intermediate for the synthesis of midpacamide and dispacamide, is described. This intermediate undergoes cyclization through the corresponding a-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 guanidine derivative provides the 2-aminoimidazole ring present in dispacamide.

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