Total Syntheses of FR-901235, Auxarthrones A-D, and Lamellicolic Anhydride.

Abstract

In our previous study, an unusual rearrangement reaction was discovered whereby dinaphthyl ketones with three hydroxy groups at restricted positions were transformed into a phenalenone ring and a benzene ring. Using the rearrangement as a key reaction, the first total syntheses of FR-901235 and auxarthrones A-D from an unstable triketone common intermediate are described. Furthermore, lamellicolic anhydride was synthesized from the triketone. This conversion is part of the putative biosynthetic pathway and was achieved experimentally for the first time.