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

研究成果: ジャーナルへの寄稿記事

82 引用 (Scopus)

抄録

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.

元の言語英語
ページ(範囲)3960-3968
ページ数9
ジャーナルJournal of Organic Chemistry
58
発行部数15
DOI
出版物ステータス出版済み - 1 1 1993

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Lewis Acids
Regioselectivity
Molecular orbitals
Orbital calculations
Anions
Salts
menthofuran
3-methylfuran
1,3-pentadiene

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

これを引用

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title = "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",
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.",
author = "Mariko Aso and Akio Ojida and Guang Yang and Cha, {Ok Ja} and Eiji Osawa and Ken Kanematsu",
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TY - JOUR

T1 - Furannulation Strategy for Synthesis of the Naturally Occurring Fused 3-Methylfurans

T2 - 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

AU - Aso, Mariko

AU - Ojida, Akio

AU - Yang, Guang

AU - Cha, Ok Ja

AU - Osawa, Eiji

AU - Kanematsu, Ken

PY - 1993/1/1

Y1 - 1993/1/1

N2 - 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.

AB - 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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