title: Synthesis of cruentaren A.
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 toward the total synthesis of cruentaren A, which led to a convergent and efficient synthesis of the natural product.
authors.affiliation: Department of Medicinal Chemistry, The University of Kansas, 1251 Wescoe Hall Drive, Malott 4070, Lawrence, Kansas 66045-7562, United States.
authors.forename: Bhaskar Reddy
authors.initials: BR
authors.lastname: Kusuma
authors.forename: Gary E L
authors.initials: GE
authors.lastname: Brandt
authors.forename: Brian S J
authors.initials: BS
authors.lastname: Blagg
mesh_terms: D000478:Alkylation; D000935:Antifungal Agents; D006801:Humans; D018942:Macrolides / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D025261:Mitochondrial Proton-Translocating ATPases / Q000037:antagonists & inhibitors; D015394:Molecular Structure; D009231:Myxococcales / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000935:Antifungal Agents; D018942:Macrolides; C516694:cruentaren A; D025261:Mitochondrial Proton-Translocating ATPases