Journal
ORGANIC LETTERS
Volume 14, Issue 24, Pages 6242-6245Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol302999v
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Funding
- NIH [CA109265]
- Madison and Lila Self Graduate Fellowship
- American Foundation for Pharmaceutical Education
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Cruentaren A, an antifungal benzolactone produced by the myxobacterium Byssovorax cruenta, is highly cytotoxic against various human cancer cell lines and a highly selective inhibitor of mitochondrial F-ATPase. A convergent and efficient synthesis of cruentaren A is reported, based upon a diastereoselective alkylation, a series of stereoselective aldol reactions utilizing Myers' pseudoephedrine propionamide, an acyl bromide mediated esterification, and a ring-closing metathesis (RCM) as the key steps. The RCM reaction was applied for the first time toward the total synthesis of cruentaren A, which led to a convergent and efficient synthesis of the natural product.
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