Stereoselective synthesis of spicigerolide

The first total synthesis of the naturally occurring, cytotoxic lactone spicigerolide is described. The commercially available sugar l-rhamnose was the chiral starting materal. Key steps in the synthesis were an aldehyde two-carbon homologation via the Corey–Fuchs protocol, an asymmetric Brown-type aldehyde allylation and a ring-closing metathesis.