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A concise synthesis of (-)-lasonolide A.

ABSTRACT: Lasonolide A is a novel polyketide displaying potent anticancer activity across a broad range of cancer cell lines. Here, an enantioselective convergent total synthesis of the (-)-lasonolide A in 16 longest linear and 34 total steps is described. This approach significantly reduces the step count compared to other known syntheses. The synthetic strategy utilizes alkyne-bearing substrates as core building blocks and is highlighted by stitching together two similarly complex halves via a key Ru-catalyzed alkene-alkyne coupling and macrolactionization.

SUBMITTER: Trost BM

PROVIDER: S-EPMC3939832 | biostudies-literature | 2014 Jan

REPOSITORIES: biostudies-literature

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A concise synthesis of (-)-lasonolide A.

Trost Barry M BM Stivala Craig E CE Hull Kami L KL Huang Audris A Fandrick Daniel R DR

Journal of the American Chemical Society 20131224 1

Lasonolide A is a novel polyketide displaying potent anticancer activity across a broad range of cancer cell lines. Here, an enantioselective convergent total synthesis of the (-)-lasonolide A in 16 longest linear and 34 total steps is described. This approach significantly reduces the step count compared to other known syntheses. The synthetic strategy utilizes alkyne-bearing substrates as core building blocks and is highlighted by stitching together two similarly complex halves via a key Ru-ca ...[more]

PMID: 24308383

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