Structural Studies of the Mycotoxin Verrucosidin

Maya Ganguli, Fayetteville State University
Leo T. Burka, National Institute of Environmental Health Sciences (NIEHS)
Thomas M. Harris, Vanderbilt University

Abstract

Structure 1 has been established for verrucosidin, a neurotoxin isolated from Penicillium verrucosum var. cyclopium. A novel fragmentation in base yields aldehyde 3 and a rearranged cyclopentenone carboxylic acid. The structure of the methyl ester 4 of this acid has been established by independent synthesis. A mechanism is proposed for the formation of the cyclopentenone ring of 4 from the epoxy ?-pyrone of 1. © 1984, American Chemical Society. All rights reserved.