4.8 Article

Total Synthesis of the Sphingolipid Biosynthesis Inhibitor Fumonisin B1

Journal

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 131, Issue 17, Pages 6066-+

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/ja9009265

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Funding

  1. National Institutes of Health
  2. National Science Foundation
  3. University Research Committee of Emory University

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The first total synthesis of the sphingolipid biosynthesis inhibitor fumonisin B, has been achieved. This convergent synthesis utilizes oxonia Cope rearrangements to prepare two key homoallylic alcohols, which are then functionatized to the primary components A and B for cross-coupling. Other highlights of our approach include a new and efficient synthesis of the diprotected tricarballylic acid C and a global deprotection strategy as the final step.

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