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Synthesis of (+)-Pancratistatins via Catalytic Desymmetrization of Benzene.

ABSTRACT: A concise synthesis of (+)-pancratistatin and (+)-7-deoxypancratistatin from benzene using an enantioselective, dearomative carboamination strategy has been achieved. This approach, in combination with the judicious choice of subsequent olefin-type difunctionalization reactions, permits rapid and controlled access to a hexasubstituted core. Finally, minimal use of intermediary steps as well as direct, late stage C-7 hydroxylation provides both natural products in six and seven operations.

SUBMITTER: Hernandez LW

PROVIDER: S-EPMC5960067 | biostudies-literature | 2017 Nov

REPOSITORIES: biostudies-literature

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Synthesis of (+)-Pancratistatins via Catalytic Desymmetrization of Benzene.

Hernandez Lucas W LW Pospech Jola J Klöckner Ulrich U Bingham Tanner W TW Sarlah David D

Journal of the American Chemical Society 20171025 44

A concise synthesis of (+)-pancratistatin and (+)-7-deoxypancratistatin from benzene using an enantioselective, dearomative carboamination strategy has been achieved. This approach, in combination with the judicious choice of subsequent olefin-type difunctionalization reactions, permits rapid and controlled access to a hexasubstituted core. Finally, minimal use of intermediary steps as well as direct, late stage C-7 hydroxylation provides both natural products in six and seven operations. ...[more]

PMID: 29059521

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