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Total synthesis of the akuammiline alkaloid picrinine.

ABSTRACT: We report the first total synthesis of the complex akuammiline alkaloid picrinine, which was first isolated nearly five decades ago. Our synthetic approach features a concise assembly of the [3.3.1]-azabicyclic core, a key Fischer indolization reaction to forge the natural product's carbon framework, and a series of delicate late-stage transformations to complete the synthesis. Our synthesis of picrinine also constitutes a formal synthesis of the related polycyclic alkaloid strictamine.

SUBMITTER: Smith JM

PROVIDER: S-EPMC3985766 | biostudies-literature | 2014 Mar

REPOSITORIES: biostudies-literature

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Total synthesis of the akuammiline alkaloid picrinine.

Smith Joel M JM Moreno Jesus J Boal Ben W BW Garg Neil K NK

Journal of the American Chemical Society 20140312 12

We report the first total synthesis of the complex akuammiline alkaloid picrinine, which was first isolated nearly five decades ago. Our synthetic approach features a concise assembly of the [3.3.1]-azabicyclic core, a key Fischer indolization reaction to forge the natural product's carbon framework, and a series of delicate late-stage transformations to complete the synthesis. Our synthesis of picrinine also constitutes a formal synthesis of the related polycyclic alkaloid strictamine. ...[more]

PMID: 24597784

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