title: Total synthesis of (-)-teucvidin.
abstract: A concise enantioselective synthesis of (-)-teucvidin has been achieved. Our synthetic strategy involved the diastereoselective Michael/Conia-ene cascade cyclization reaction for rapid establishment of the cis-decalin skeleton with three new stereogenic centers in one pot (72%, single diastereomer), the epoxidation/dealkoxycarbonylation protocol for construction of the fused furanone moiety, and the O-allylation/Claisen rearrangement protocol for construction of the all-carbon quaternary center at C9 of the clerodane skeleton.
authors.affiliation: Laboratory of Chemical Genomics, School of Chemical Biology and Biotechnology, Peking University Shenzhen Graduate School, Shenzhen University Town, Xili, Shenzhen 518055, China.
authors.forename: Xiaozu
authors.initials: X
authors.lastname: Liu
authors.forename: Chi-Sing
authors.initials: CS
authors.lastname: Lee
mesh_terms: D002384:Catalysis; D003500:Cyclization; D045785:Diterpenes, Clerodane / Q000138:chemical synthesis* / Q000737:chemistry; D019686:Lamiaceae / Q000737:chemistry; D015394:Molecular Structure; D009281:Naphthalenes / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D045785:Diterpenes, Clerodane; D009281:Naphthalenes; C574682:teucvidin; C007229:decalin