Progress towards total synthesis of rapiculine

Abstract

Rapiculine, isolated in 1991 by Udagawa and coworkers from the culture filtrate of Ramichloridium apiculatum incubated in Czapek-Dox medium, has structurally unique 1-decalone derivatives bearing six contiguous stereocenters, with no previous synthetic studies reported. A close retrosynthetic analysis indicated that the cycloadduct of 3,5-dibromo-2-pyrone with methyl vinyl ketone would readily provide the core decaline framework. Presented here is our recent effort towards total synthesis of rapiculine