title: Stereoselective total synthesis of (-)-kumausallene.
abstract: A stereoselective total synthesis of (-)-kumausallene was completed in 12 steps from acetylacetone. The hidden symmetry of (-)-kumausallene was recognized, and its skeleton was constructed efficiently from a C(2)-symmetric diol by a palladium-catalyzed cascade reaction. High diastereoselectivity was observed for the DMF-promoted biomimetic 1,4-bromocyclization of a conjugated enyne.
authors.affiliation: School of Pharmacy and Department of Chemistry, University of Wisconsin, Madison, Wisconsin 53705, USA.
authors.forename: Jenny B
authors.initials: JB
authors.lastname: Werness
authors.forename: Weiping
authors.initials: W
authors.lastname: Tang
mesh_terms: D002384:Catalysis; D003500:Cyclization; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry*; D012717:Sesquiterpenes / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D012717:Sesquiterpenes; C561696:kumausallene; D010165:Palladium