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

1976; Taylor & Francis; Volume: 6; Issue: 5 Linguagem: Inglês

10.1080/00397917608063533

1532-2432

Shuji Takahashi,

Biological Activity of Diterpenoids and Biflavonoids

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.