Furannulation Strategy for Synthesis of the Naturally Occurring Fused 3-Methylfurans: Efficient Synthesis of Evodone and Menthofuran and Regioselective Synthesis of Maturone via a Lewis Acid Catalyzed Diels-Alder Reaction. Some Comments for Its Mechanistic Aspects

Mariko Aso, Akio Ojida, Guang Yang, Ok Ja Cha, Eiji Osawa, Ken Kanematsu

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93 Citations (Scopus)

Abstract

Fused 3-methylfurans are readily obtained by the reaction of allenic sulfonium salt 1 and the enolate anions of cyclic 1,3-dicarbonyl compounds in two steps. Using these fused 3-methylfuran compounds as intermediates, furanoterpenoids such as menthofuran (8) and evodone (4b) are synthesized efficiently. Moreover, maturone (15) is also obtained regioselectivity by Lewis acid catalyzed Diels-Alder reaction of benzofuranquinone (12) with piperylene. In the context with the regioselectivity observed in the Diels-Alder reaction of 12, semiempirical molecular orbital calculations are applied to gain its theoretical interpretation based upon frontier molecular orbital theory and transition state analysis.

Original languageEnglish
Pages (from-to)3960-3968
Number of pages9
JournalJournal of Organic Chemistry
Volume58
Issue number15
DOIs
Publication statusPublished - Jan 1 1993

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

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