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Total Synthesis of Gelsenicine via a Catalyzed Cycloisomerization Strategy.

ABSTRACT: The first total synthesis of (±)-gelsenicine is reported. The synthetic route is highly efficient (13 steps), featuring (1) a pivotal metal-catalyzed isomerization/rearrangement process that forges the central core of the molecule and (2) two facile C-N bond-forming steps that establish the flanking heterocycles.

SUBMITTER: Newcomb ET

PROVIDER: S-EPMC4732274 | biostudies-literature | 2016 Jan

REPOSITORIES: biostudies-literature

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Total Synthesis of Gelsenicine via a Catalyzed Cycloisomerization Strategy.

Newcomb Eric T ET Knutson Phil C PC Pedersen Blaine A BA Ferreira Eric M EM

Journal of the American Chemical Society 20151230 1

The first total synthesis of (±)-gelsenicine is reported. The synthetic route is highly efficient (13 steps), featuring (1) a pivotal metal-catalyzed isomerization/rearrangement process that forges the central core of the molecule and (2) two facile C-N bond-forming steps that establish the flanking heterocycles. ...[more]

PMID: 26716762

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