4.8 Article

Total Synthesis and Structural Confirmation of Brevisamide, a New Marine Cyclic Ether Alkaloid from the Dinoflagellate Karenia brevis

Journal

ORGANIC LETTERS
Volume 11, Issue 1, Pages 217-220

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/ol802426v

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Funding

  1. NIEHS NIH HHS [P01 ES 10594, P01 ES010594, P01 ES010594-08] Funding Source: Medline
  2. NATIONAL INSTITUTE OF ENVIRONMENTAL HEALTH SCIENCES [P01ES010594] Funding Source: NIH RePORTER

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The first total synthesis of brevisamide (1) has been accomplished in 21 linear steps starting from cis-but-2-ene-1,4-diol. A synthetic highlight is the Suzuki-Miyaura coupling between an ether ring fragment and a dienol side chain. This result confirmed the structure of 1 isolated from the dinoflagellate Karenia brevis.

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