First Total Synthesis of Antimitotic Compound, (+)-Phomopsidin

Takahiro Suzuki; Kenji Usui; Yoshiharu Miyake; Michio Namikoshi; Masahisa Nakada

doi:10.1021/ol036338q

First Total Synthesis of Antimitotic Compound, (+)-Phomopsidin

Takahiro Suzuki, Kenji Usui, Yoshiharu Miyake, Michio Namikoshi, Masahisa Nakada

先進理工学部

研究成果: Article › 査読

36 被引用数 (Scopus)

抄録

(Equation presented) The first total synthesis of (+)-phomopsidin has been achieved via a diastereoselective transannular Diels-Alder (TADA) reaction. Key steps in the synthesis include diastereoselective ynone reduction with (-)-α-pinene and 9-BBN, macrocyclization by E-selective intramolecular Horner-Wadsworth-Emmons (HWE) reaction, as well as carbometalation under Wipf's conditions, followed by HWE reaction at low temperature to selectively construct the (E)-1-methylpropenyl and (1E,2E)-4-carboxy-1,3-butadienyl substituents.

本文言語	English
ページ（範囲）	553-556
ページ数	4
ジャーナル	Organic Letters
巻	6
号	4
DOI	https://doi.org/10.1021/ol036338q
出版ステータス	Published - 2004 2 19

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/ol036338q

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引用スタイル

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abstract = "(Equation presented) The first total synthesis of (+)-phomopsidin has been achieved via a diastereoselective transannular Diels-Alder (TADA) reaction. Key steps in the synthesis include diastereoselective ynone reduction with (-)-α-pinene and 9-BBN, macrocyclization by E-selective intramolecular Horner-Wadsworth-Emmons (HWE) reaction, as well as carbometalation under Wipf's conditions, followed by HWE reaction at low temperature to selectively construct the (E)-1-methylpropenyl and (1E,2E)-4-carboxy-1,3-butadienyl substituents.",

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AU - Suzuki, Takahiro

AU - Usui, Kenji

AU - Miyake, Yoshiharu

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AU - Nakada, Masahisa

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