title: Controlling the facial selectivity of asymmetric [4+2] cyclo-additions: a concise synthesis of the cis-decalin core structure of superstolides A and B.
abstract: Regio-, stereo-, and facial selective [4 + 2] cycloadditions between highly activated vinyl sulfones and 1,3-dienes derived from (R)-4-tert-butyldimethylsilyloxy-2-cyclohexen-1-one provide a powerful approach for the asymmetric synthesis of compounds containing the bicyclo[2.2.2]octanone carbon skeleton. This new methodology has been successfully applied to the asymmetric synthesis of the cis-decalin core structure of the potent anticancer marine natural products superstolides A and B.
authors.affiliation: Division of Medicinal and Natural Products Chemistry, Department of Pharmaceutical Sciences and Experimental Therapeutics, College of Pharmacy, The University of Iowa, Iowa City, Iowa 52242, USA
authors.forename: Lei
authors.initials: L
authors.lastname: Chen
authors.forename: Zhengmao
authors.initials: Z
authors.lastname: Hua
authors.forename: Gangqin
authors.initials: G
authors.lastname: Li
authors.forename: Zhendong
authors.initials: Z
authors.lastname: Jin
mesh_terms: D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D001688:Biological Products / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D002384:Catalysis; D003512:Cyclohexanones / Q000737:chemistry*; D018942:Macrolides / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D008386:Marine Biology; D015394:Molecular Structure; D009281:Naphthalenes / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D012821:Silanes / Q000737:chemistry*; D013237:Stereoisomerism; D013450:Sulfones / Q000737:chemistry; D013764:Tetrahydronaphthalenes / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology
chemical_list: C561209:(R)-4-tert-butyldimethylsilyloxy-2-cyclohexen-1-one; D000970:Antineoplastic Agents; D001688:Biological Products; D003512:Cyclohexanones; D018942:Macrolides; D009281:Naphthalenes; D012821:Silanes; D013450:Sulfones; D013764:Tetrahydronaphthalenes; C091984:superstolide A; C091985:superstolide B; C009873:divinyl sulfone; C007229:decalin