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De novo asymmetric synthesis of D- and L-swainsonine.

ABSTRACT: [reaction: see text] The enantioselective syntheses of both enantiomers of the indolizidine natural product swainsonine have been achieved in 13 steps from furan. The indolizidine ring system is installed by a one-pot hydrogenolysis of both an azide and an O-Bn group along with an intramolecular reductive amination reaction. The asymmetry of swainsonine was introduced by Noyori reduction of an acylfuran. This route relies upon an Achmatowicz rearrangement, a diastereoselective palladium-catalyzed glycosylation, Luche reduction, and a dihydroxylation reaction.

SUBMITTER: Guo H

PROVIDER: S-EPMC2531217 | biostudies-literature | 2006 Apr

REPOSITORIES: biostudies-literature

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De novo asymmetric synthesis of D- and L-swainsonine.

Guo Haibing H O'Doherty George A GA

Organic letters 20060401 8

[reaction: see text] The enantioselective syntheses of both enantiomers of the indolizidine natural product swainsonine have been achieved in 13 steps from furan. The indolizidine ring system is installed by a one-pot hydrogenolysis of both an azide and an O-Bn group along with an intramolecular reductive amination reaction. The asymmetry of swainsonine was introduced by Noyori reduction of an acylfuran. This route relies upon an Achmatowicz rearrangement, a diastereoselective palladium-catalyze ...[more]

PMID: 16597122

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