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

被引：7
|
作者：
Shiina, I [1 ]
Uchimaru, T
Shoji, M
Kakeya, H
Osada, H
Hayashi, Y
机构：
[1] Tokyo Univ Sci, Fac Sci, Dept Appl Chem, Shinjuku Ku, Tokyo 1628601, Japan
[2] Tokyo Univ Sci, Fac Engn, Dept Ind Chem, Shinjuku Ku, Tokyo 1628601, Japan
[3] Natl Inst Adv Ind Sci & Technol, Res Inst Computat Sci, Tsukuba, Ibaraki 3058658, Japan
[4] RIKEN, Discovery Res Inst, Antibiot Lab, Wako, Saitama 3510198, Japan
来源：
ORGANIC LETTERS | 2006年 / 8卷 / 06期
关键词：
D O I：
10.1021/ol052916m
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
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.
引用
收藏
页码：1041 / 1044
页数：4
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