Synthesis of pinguisane-type sesquiterpenoids acutifolone A, pinguisenol, and bisacutifolones by a Diels-Alder dimerization reaction

Junichi Shiina; Masataka Oikawa; Kensuke Nakamura; Rika Obata; Shigeru Nishiyama

doi:10.1002/ejoc.200700522

Synthesis of pinguisane-type sesquiterpenoids acutifolone A, pinguisenol, and bisacutifolones by a Diels-Alder dimerization reaction

Junichi Shiina, Masataka Oikawa, Kensuke Nakamura, Rika Obata, Shigeru Nishiyama

研究成果: Article › 査読

20 被引用数 (Scopus)

抄録

The total synthesis of pinguisane-type sesquiterpenoids, acutifolone A (1) and pinguisenol (2), has been achieved by using the Mukaiyama aldol reaction as the key step. The intermolecular Diels-Alder reaction of these monomelic natural products successfully led to stereoselective dimerization, leading to bisacutifolones A (3) and B (4). Theoretical calculations revealed that the dimerization reaction proceeded through the most stable transition state.

本文言語	English
ページ（範囲）	5190-5197
ページ数	8
ジャーナル	European Journal of Organic Chemistry
号	31
DOI	https://doi.org/10.1002/ejoc.200700522
出版ステータス	Published - 2007
外部発表	はい

ASJC Scopus subject areas

物理化学および理論化学
有機化学

文献へのアクセス

10.1002/ejoc.200700522

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引用スタイル

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abstract = "The total synthesis of pinguisane-type sesquiterpenoids, acutifolone A (1) and pinguisenol (2), has been achieved by using the Mukaiyama aldol reaction as the key step. The intermolecular Diels-Alder reaction of these monomelic natural products successfully led to stereoselective dimerization, leading to bisacutifolones A (3) and B (4). Theoretical calculations revealed that the dimerization reaction proceeded through the most stable transition state.",

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T1 - Synthesis of pinguisane-type sesquiterpenoids acutifolone A, pinguisenol, and bisacutifolones by a Diels-Alder dimerization reaction

AU - Shiina, Junichi

AU - Oikawa, Masataka

AU - Nakamura, Kensuke

AU - Obata, Rika

AU - Nishiyama, Shigeru

PY - 2007

Y1 - 2007

N2 - The total synthesis of pinguisane-type sesquiterpenoids, acutifolone A (1) and pinguisenol (2), has been achieved by using the Mukaiyama aldol reaction as the key step. The intermolecular Diels-Alder reaction of these monomelic natural products successfully led to stereoselective dimerization, leading to bisacutifolones A (3) and B (4). Theoretical calculations revealed that the dimerization reaction proceeded through the most stable transition state.

AB - The total synthesis of pinguisane-type sesquiterpenoids, acutifolone A (1) and pinguisenol (2), has been achieved by using the Mukaiyama aldol reaction as the key step. The intermolecular Diels-Alder reaction of these monomelic natural products successfully led to stereoselective dimerization, leading to bisacutifolones A (3) and B (4). Theoretical calculations revealed that the dimerization reaction proceeded through the most stable transition state.

KW - Autoxidation

KW - Biomimetic synthesis

KW - Liverwort

KW - Terpenoids

KW - Total synthesis

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