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Total synthesis of fellutamide B and deoxy-fellutamides B, C, and D.

ABSTRACT: The total syntheses of the marine-derived lipopeptide natural product fellutamide B and deoxy-fellutamides B, C, and D are reported. These compounds were accessed through a novel solid-phase synthetic strategy using Weinreb amide-derived resin. As part of the synthesis, a new enantioselective route to (3R)-hydroxy lauric acid was developed utilizing a Brown allylation reaction followed by an oxidative cleavage-oxidation sequence as the key steps. The activity of these natural products, and natural product analogues was also assessed against Mycobacterium tuberculosis in vitro.

SUBMITTER: Giltrap AM

PROVIDER: S-EPMC3736429 | biostudies-literature | 2013 Jul

REPOSITORIES: biostudies-literature

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Total synthesis of fellutamide B and deoxy-fellutamides B, C, and D.

Giltrap Andrew M AM Cergol Katie M KM Pang Angel A Britton Warwick J WJ Payne Richard J RJ

Marine drugs 20130708 7

The total syntheses of the marine-derived lipopeptide natural product fellutamide B and deoxy-fellutamides B, C, and D are reported. These compounds were accessed through a novel solid-phase synthetic strategy using Weinreb amide-derived resin. As part of the synthesis, a new enantioselective route to (3R)-hydroxy lauric acid was developed utilizing a Brown allylation reaction followed by an oxidative cleavage-oxidation sequence as the key steps. The activity of these natural products, and natur ...[more]

PMID: 23880930

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