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New syntheses of (±)-tashiromine and (±)-epitashiromine via enaminone intermediates.

ABSTRACT: The syntheses of the naturally occurring indolizidine alkaloid (±)-tashiromine and its unnatural epimer (±)-epitashiromine are demonstrated through the use of enaminone chemistry. The impact of various electron-withdrawing substituents at the C-8 position of the indolizidine core on the preparation of the bicyclic system is described.

SUBMITTER: Riley DL

PROVIDER: S-EPMC5238587 | biostudies-literature | 2016

REPOSITORIES: biostudies-literature

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New syntheses of (±)-tashiromine and (±)-epitashiromine via enaminone intermediates.

Riley Darren L DL Michael Joseph P JP de Koning Charles B CB

Beilstein journal of organic chemistry 20161202

The syntheses of the naturally occurring indolizidine alkaloid (±)-tashiromine and its unnatural epimer (±)-epitashiromine are demonstrated through the use of enaminone chemistry. The impact of various electron-withdrawing substituents at the C-8 position of the indolizidine core on the preparation of the bicyclic system is described. ...[more]

PMID: 28144330

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