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. 2016 Feb 5;18(3):360-3.
doi: 10.1021/acs.orglett.5b03285. Epub 2016 Jan 12.

Enantioselective Total Syntheses of Kuwanon X, Kuwanon Y, and Kuwanol A

Lei Gao  1   2 , Jianguang Han  2 , Xiaoguang Lei  1   2   3
Affiliations

Enantioselective Total Syntheses of Kuwanon X, Kuwanon Y, and Kuwanol A

Lei Gao et al. Org Lett. .

Abstract

The first enantioselective total syntheses of (-)-kuwanon X, (+)-kuwanon Y, and (+)-kuwanol A have been accomplished by using asymmetric Diels-Alder cycloaddition promoted by chiral VANOL or VAPOL/boron Lewis acid. The biosynthesis-inspired asymmetric Diels-Alder cycloaddition shows high exo selectivity (exo/endo = 13/1), which was unprecedented in the previous total syntheses of related prenylflavonoid Diels-Alder natural products. An acid catalyzed intramolecular ketalization process enabled a biomimetic transformation to construct the polycyclic skeleton of kuwanol A efficiently.

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