title: Total syntheses of cannabicyclol, clusiacyclol A and B, iso-eriobrucinol A and B, and eriobrucinol.
abstract: Total syntheses of a series of chromane natural products that contain a cyclobutane ring are described. A unified theme in the strategy employed for all these syntheses is an oxa-[3 + 3] annulation for constructing the chromane nucleus and a stepwise cationic [2 + 2] cycloaddition for the cyclobutane formation. More importantly, the two reactions could be rendered in tandem, thereby providing an expeditious approach to this family of natural products.
authors.affiliation: Division of Pharmaceutical Sciences and Department of Chemistry, University of Wisconsin , Madison, Wisconsin 53705, United States, and School of Pharmaceutical Science and Technology, Tianjin University , Tianjin, 300072, P. R. China.
authors.forename: Hyun-Suk
authors.initials: HS
authors.lastname: Yeom
authors.forename: Hui
authors.initials: H
authors.lastname: Li
authors.forename: Yu
authors.initials: Y
authors.lastname: Tang
authors.forename: Richard P
authors.initials: RP
authors.lastname: Hsung
mesh_terms: D001688:Biological Products / Q000138:chemical synthesis* / Q000737:chemistry; D002186:Cannabinoids / Q000138:chemical synthesis* / Q000737:chemistry; D002839:Chromans / Q000138:chemical synthesis* / Q000737:chemistry; D061565:Cycloaddition Reaction; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D001688:Biological Products; D002186:Cannabinoids; D002839:Chromans; C000588627:clusiacyclol A; C000588628:clusiacyclol B; C022213:cannabicyclol