A stereoselective synthesis of platyphyllide

Abstract

The norsesquiterpene lactone, platyphyllide has been synthesized in 8 steps in 23% overall yield via the Diels-Alder adduct of 2-(4-methylpent-3-enyl)furan with dimethyl acetylenedicarboxylate, the 3-substituted phthalic diester, and an o-formylbenzamide. An intramolecular ene reaction established the skeleton, and the final step involved inversion of configuration at the benzylic site.