4.8 Article

A Concise, Biomimetic Total Synthesis of (+)-Davanone

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ORGANIC LETTERS
卷 11, 期 10, 页码 2217-2218

出版社

AMER CHEMICAL SOC
DOI: 10.1021/ol900697w

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资金

  1. Camille and Henry Dreyfus Foundation Faculty Startup Award
  2. National Science Foundation REU [CHE-0353662]
  3. Beckman Foundation
  4. Harvey Mudd College (HMC)
  5. Pomona College Chemistry Departments
  6. Christian Scholars Foundation
  7. Pfizer Summer Undergraduate Research Fellowships

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A concise, biomimetic synthesis of the antifungal and antispasmodic natural product (+)-davanone is described. The key stereoselective reactions are a Sharpless asymmetric epoxidation, a thiazolium-catalyzed esterification, and a palladium-mediated cyclization. All carbons are derived from isoprene units and no protecting groups are used, permitting an atom- and redox-economical synthesis.

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