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Biomimetic Approach to the Catalytic Enantioselective Synthesis of Flavonoids.

ABSTRACT: Herein is reported the direct asymmetric addition of phenol nucleophiles to benzopyrylium salts as a means to produce enantioenriched flavonoid-like compounds. This enantioselective C-C bond construction was achieved through a chiral anion phase-transfer strategy that mimics the proposed biosynthesis of this structurally diverse set of natural products. The utility of this methodology was demonstrated in enantioselective synthesis of a 2,8-dioxabicyclo[3.3.1]nonane and a 2,4-diarylbenzopyran.

SUBMITTER: Yang Z

PROVIDER: S-EPMC5149420 | biostudies-literature | 2016 Aug

REPOSITORIES: biostudies-literature

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Biomimetic Approach to the Catalytic Enantioselective Synthesis of Flavonoids.

Yang Zhenyu Z He Ying Y Toste F Dean FD

Journal of the American Chemical Society 20160729 31

Herein is reported the direct asymmetric addition of phenol nucleophiles to benzopyrylium salts as a means to produce enantioenriched flavonoid-like compounds. This enantioselective C-C bond construction was achieved through a chiral anion phase-transfer strategy that mimics the proposed biosynthesis of this structurally diverse set of natural products. The utility of this methodology was demonstrated in enantioselective synthesis of a 2,8-dioxabicyclo[3.3.1]nonane and a 2,4-diarylbenzopyran. ...[more]

PMID: 27472195

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