4.8 Article

A Concise Synthesis of (-)-Lasonolide A

Journal

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 136, Issue 1, Pages 88-91

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/ja411270d

Keywords

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Funding

  1. NIH [GM33049]
  2. NIH Ruth L. Kirschstein National Research Service Awards [GM101747, GM086093, GM077840]

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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.

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