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Stereocontrolled construction of six vicinal stereogenic centers on a hexahydroxanthone framework through a formal [2+1+3] annulation

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Abstract

The first example of a bifunctional donor–donor 3C synthon in situ from activated methine (methyleneindolinone and methylenebenzofuranone) with nitromethane through a [2+1] Michael addition, which further directed the following organocascade Michael/Henry cycloaddition reaction in a one-pot operation is developed, serving as a fruitful strategy for facile access to optically active and structurally diverse hexahydroxanthones with up to six contiguous stereocenters, including a quaternary one. A series of diversely functionalized products are smoothly obtained with up to 76% yield, >20 : 1 d.r. and 98% ee from simple and readily available starting materials. In addition, this is the first example of 3-formyl chromone as an acceptor–acceptor 3C building block, and also the first asymmetric catalytic construction of six vicinal stereogenic centers on a hexahydroxanthone scaffold.

Graphical abstract: Stereocontrolled construction of six vicinal stereogenic centers on a hexahydroxanthone framework through a formal [2+1+3] annulation

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Publication details

The article was received on 15 Oct 2019, accepted on 22 Oct 2019 and first published on 22 Oct 2019


Article type: Communication
DOI: 10.1039/C9CC08101A
Chem. Commun., 2019, Advance Article

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    Stereocontrolled construction of six vicinal stereogenic centers on a hexahydroxanthone framework through a formal [2+1+3] annulation

    S. Chang, X. Zou, Y. Gong, X. He, X. Liu and Y. Zhou, Chem. Commun., 2019, Advance Article , DOI: 10.1039/C9CC08101A

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