title: Total synthesis of (-)-anisatin.
abstract: A novel synthetic route to (-)-anisatin has been developed. Our synthesis features a rhodium-catalyzed 1,4-addition of an arylboronic acid, an intramolecular Diels-Alder reaction of an ortho-quinone monoketal, a stereoselective [2,3]-Wittig rearrangement, and construction of the oxabicyclo [3.3.1] skeleton via cleavage of an epoxide by a primary amide.
authors.affiliation: Graduate School of Pharmaceutical Sciences, University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033, Japan.
authors.forename: Akihiro
authors.initials: A
authors.lastname: Ogura
authors.forename: Kohei
authors.initials: K
authors.lastname: Yamada
authors.forename: Satoshi
authors.initials: S
authors.lastname: Yokoshima
authors.forename: Tohru
authors.initials: T
authors.lastname: Fukuyama
mesh_terms: D002384:Catalysis; D003500:Cyclization; D029523:Illicium / Q000737:chemistry; D007783:Lactones / Q000138:chemical synthesis* / Q000737:chemistry; D010084:Oxidation-Reduction; D011809:Quinones / Q000737:chemistry; D012238:Rhodium / Q000737:chemistry; D012717:Sesquiterpenes / Q000138:chemical synthesis* / Q000737:chemistry; D013141:Spiro Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D007783:Lactones; D011809:Quinones; D012717:Sesquiterpenes; D013141:Spiro Compounds; D012238:Rhodium; C031244:anisatin