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.
No takes yet. Share an insight, caveat, or question.
Ganguli et al. (1984) studied this question.