Asymmetric synthesis of 9-alkyl tetrahydroxanthenones via tandem asymmetric Michael/cyclization promoted by chiral phosphoric acid

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Asymmetric synthesis of 9-alkyl tetrahydroxanthenones via tandem asymmetric Michael/cyclization promoted by chiral phosphoric acid

Gao, Yu-Qi; Hou, Yi; Chen, Junhan; Zhen, Yanxia; Xu, Dongyang; Zhang, Hongli; Wei, Hongbo; Xie, Weiqing

Organic & biomolecular chemistry, 01/2021, Volume: 19, Issue: 2

Journal Article

A tandem asymmetric Michael-addition/cyclization of cyclic 1,3-dicarbonyl compounds to β,γ-unsaturated α-ketoesters catalyzed by chiral phosphoric acid is presented. This protocol provides a facile approach for the construction of enantioenriched 9-alkyl tetrahydroxanthenones, an ubiquitous framework found in a number of natural products and pharmaceutical molecules, in high yields with good to high enantioselectivities.

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