Stereoselective synthesis of spicigerolide

✍ Scribed by Eva Falomir; Juan Murga; Miguel Carda; J.Alberto Marco

• Book ID: 104252689
• Publisher: Elsevier Science
• Year: 2003
• Tongue: French
• Weight: 166 KB
• Volume: 44
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(02)02588-1

✦ Synopsis

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.