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

Organic Letters
Isamu ShiinaYujiro Hayashi

Abstract

[reaction: see text] 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.

References

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Oct 9, 2002·Angewandte Chemie·Mitsuru ShojiYujiro Hayashi
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May 19, 2005·Chemical Communications : Chem Comm·Hideaki KakeyaHiroyuki Osada

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Citations

May 26, 2007·The Journal of Physical Chemistry. a·Mireia GüellMiquel Solà

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