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Synthesis of Cruentaren A
Kusuma, Bhaskar Reddy Brandt, Gary E. L. Blagg, Brian S. J.
Kusuma, Bhaskar Reddy
Brandt, Gary E. L.
Blagg, Brian S. J.
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Abstract
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 towards the total synthesis of cruentaren A, which led to a convergent and efficient synthesis of the natural product.
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2012-12-21
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American Chemical Society
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Kusuma, B. R., Brandt, G. E. L., & Blagg, B. S. J. (2012). Synthesis of Cruentaren A. Organic Letters, 14(24), 6242–6245. http://doi.org/10.1021/ol302999v