Total Synthesis of Nominal ent-Chlorabietol B.

Abstract

The nominal enantiomer of chlorabietol B was regio- and stereoselectively synthesized from (-)-abietic acid in 13 steps. Key features of the synthesis involved an oxidative [3+2] cycloaddition to install the dihydrobenzofuran moiety and an Aldol reaction, followed by elimination and reduction steps to introduce the long chain with three cis double bonds. However, obvious differences in the NMR spectra of the synthetic and natural samples suggested that the proposed structure of chlorabietol B should be revised carefully.