Journal
ORGANIC LETTERS
Volume 11, Issue 10, Pages 2217-2218Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol900697w
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Funding
- Camille and Henry Dreyfus Foundation Faculty Startup Award
- National Science Foundation REU [CHE-0353662]
- Beckman Foundation
- Harvey Mudd College (HMC)
- Pomona College Chemistry Departments
- Christian Scholars Foundation
- 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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