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Total synthesis of 6-deoxyerythronolide B via C-C bond-forming transfer hydrogenation.

ABSTRACT: The 14-membered macrolide 6-deoxyerythronolide B is prepared in 14 steps (longest linear sequence) and 20 total steps. Two different methods for alcohol CH-crotylation via transfer hydrogenation are deployed for the first time in target-oriented synthesis. Enyne metathesis is used to form the 14-membered ring. The present approach represents the most concise construction of any erythronolide reported, to date.

SUBMITTER: Gao X

PROVIDER: S-EPMC3625983 | biostudies-literature | 2013 Mar

REPOSITORIES: biostudies-literature

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Total synthesis of 6-deoxyerythronolide B via C-C bond-forming transfer hydrogenation.

Gao Xin X Woo Sang Kook SK Krische Michael J MJ

Journal of the American Chemical Society 20130306 11

The 14-membered macrolide 6-deoxyerythronolide B is prepared in 14 steps (longest linear sequence) and 20 total steps. Two different methods for alcohol CH-crotylation via transfer hydrogenation are deployed for the first time in target-oriented synthesis. Enyne metathesis is used to form the 14-membered ring. The present approach represents the most concise construction of any erythronolide reported, to date. ...[more]

PMID: 23464668

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