Furannulation strategy for synthesis of the naturally occurring fused 3-methylfurans: efficient synthesis of evodone and menthofuran and regioselective synthesis of …

…, G Yang, OJ Cha, E Osawa, K Kanematsu

Index: Aso; Ojida; Yang; Cha; Osawa; Kanematsu Journal of Organic Chemistry, 1993 , vol. 58, # 15 p. 3960 - 3968

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Citation Number: 70

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) ...