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

被引:100
作者
ASO, M
OJIDA, A
YANG, G
CHA, OJ
OSAWA, E
KANEMATSU, K
机构
[1] KYUSHU UNIV 62,FAC PHARMACEUT SCI,INST SYNTHET ORGAN CHEM,HIGASHI KU,FUKUOKA 812,JAPAN
[2] TOYOHASHI UNIV TECHNOL,DEPT KNOWLEDGE BASED INFORMAT ENGN,TOYOHASHI 441,JAPAN
关键词
D O I
10.1021/jo00067a031
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
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.
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页码:3960 / 3968
页数:9
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