Asymmetric Total Synthesis of Euphordraculoate A and Pedrolide

Abstract

Here we report the asymmetric total syntheses of two rearranged tigliane diterpenoids, euphordraculoate A and pedrolide. A reductive dihydroxylation cascade and Nazarov cyclization were performed to generate euphordraculoate A, which was subjected to a cascade of Eu-promoted dienyl enolization, intramolecular Diels-Alder reaction and enol-ketone tautomerization to afford pedrolide, a pathway consistent with our proposal for the biogenesis of pedrolide.

Keywords: Asymmetric total synthesis; Cascade reactions; IMDA reaction; Nazarov cyclization; rearranged tigliane diterpenoids.