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Tandem C-H oxidation/cyclization/rearrangement and its application to asymmetric syntheses of (-)-brussonol and (-)-przewalskine E.

ABSTRACT: Natural products are a vital source of lead compounds in drug discovery. Development of efficient tandem reactions to build useful compounds and apply them to the synthesis of natural products is not only a significant challenge but also an important goal for chemists. Here we describe a tandem C-H oxidation/cyclization/rearrangement of isochroman-derived allylic silylethers, promoted by DDQ and InCl3. This method allows the efficient construction of tricyclic benzoxa[3.2.1]octanes with a wide substrate scope. We employ this tandem reaction to achieve the asymmetric total syntheses of (-)-brussonol and (-)-przewalskine E.

SUBMITTER: Jiao ZW

PROVIDER: S-EPMC4557391 | biostudies-literature | 2015 Jun

REPOSITORIES: biostudies-literature

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Tandem C-H oxidation/cyclization/rearrangement and its application to asymmetric syntheses of (-)-brussonol and (-)-przewalskine E.

Jiao Zhi-Wei ZW Tu Yong-Qiang YQ Zhang Qing Q Liu Wen-Xing WX Zhang Shu-Yu SY Wang Shao-Hua SH Zhang Fu-Min FM Jiang Sen S

Nature communications 20150617

Natural products are a vital source of lead compounds in drug discovery. Development of efficient tandem reactions to build useful compounds and apply them to the synthesis of natural products is not only a significant challenge but also an important goal for chemists. Here we describe a tandem C-H oxidation/cyclization/rearrangement of isochroman-derived allylic silylethers, promoted by DDQ and InCl3. This method allows the efficient construction of tricyclic benzoxa[3.2.1]octanes with a wide s ...[more]

PMID: 26081438

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