New Synthetic Route to 3-Substituted Furans; Synthesis of Perillene and Dendrolasin

Abstract

Perillene (I) and dendrolasin (II) are naturally occurring furanoid terpenes and have been previously synthesized starting from furans by Thomas in 1970,¹, Johnson in 1969² and Vig in 1975³, and also from non-furanoid precursors by Spencer in 1974⁴ and Kondo in 1976⁵. We describe herein the synthesis of the title compounds, 3-substituted furans, via unsaturated lactones from nonfuranoid intermediates shown in the Scheme. This synthetic method, utilizing the modified Wittig reaction⁶ in the key step, must be useful for synthesis of 3,4-disubstituted furans.