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