Computational study on the reaction mechanism of the key thermal [4 + 4] cycloaddition reaction in the biosynthesis of epoxytwinol A

Isamu Shiina; Tadafumi Uchimaru; Mitsuru Shoji; Hideaki Kakeya; Hiroyuki Osada; Yujiro Hayashi

doi:10.1021/ol052916m

Computational study on the reaction mechanism of the key thermal [4 + 4] cycloaddition reaction in the biosynthesis of epoxytwinol A

Isamu Shiina, Tadafumi Uchimaru, Mitsuru Shoji, Hideaki Kakeya, Hiroyuki Osada, Yujiro Hayashi

薬科学科

研究成果: Article › 査読

11 被引用数 (Scopus)

抄録

The key [4 + 4] cycloaddition in the biosynthesis of epoxytwinol A has been established by theoretical calculations to comprise of three processes. The first step is formation of the C8-C8′ bond generating a biradical intermediate. Next, rotation about the C8-C8′ bond occurs, and finally the C1-C1′ bond is formed. Biradicals stabilized by conjugation and two hydrogen bonds are essential for realization of this rare thermal [4 + 4] cycloaddition.

本文言語	English
ページ（範囲）	1041-1044
ページ数	4
ジャーナル	Organic Letters
巻	8
号	6
DOI	https://doi.org/10.1021/ol052916m
出版ステータス	Published - 2006 3月 16

ASJC Scopus subject areas

生化学
物理化学および理論化学
有機化学

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10.1021/ol052916m

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引用スタイル

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AU - Kakeya, Hideaki

AU - Osada, Hiroyuki

AU - Hayashi, Yujiro

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