title: Total Syntheses of (±)-Rhodonoids A and B and C12-epi-Rhodonoid B.
abstract: Total syntheses of (±)-rhodonoids A and B and C12-epi-rhodonoid B are described here. A unified strategy employed in these syntheses is an intramolecular oxa-[3 + 3] annulation for accessing the chromene unit. A Fe(OTf)3-promoted diastereoselective cationic [2 + 2] cycloaddition and a photochemical [2 + 2] cycloaddition were featured to construct the cyclobutane core of (±)-rhodonoids A and B and C12-epi-rhodonoid B, respectively. Fe(OTf)3also leads to an interesting bridged tetracycle, which was unambiguously confirmed by single crystal X-ray analysis.
authors.affiliation: School of Pharmaceutical Science and Technology, Tianjin University , Tianjin, 300072 P. R. China.
authors.forename: Hao
authors.initials: H
authors.lastname: Wu
authors.affiliation: School of Pharmacy, University of Wisconsin , Madison, Wisconsin 53705, United States.
authors.forename: Richard P
authors.initials: RP
authors.lastname: Hsung
authors.affiliation: School of Pharmaceutical Science and Technology, Tianjin University , Tianjin, 300072 P. R. China.|Key Laboratory of Marine Drugs, Chinese Ministry of Education, School of Medicine and Pharmacy, Ocean University of China , 5 Yushan Road, Qingdao 266003, China.|Laboratory for Marine Drugs and Bioproducts, Qingdao National Laboratory for Marine Science and Technology , Qingdao 266237, P. R. China.
authors.forename: Yu
authors.identifier: 0000-0001-8224-4639
authors.initials: Y
authors.lastname: Tang
mesh_terms: D015394:Molecular Structure; D013237:Stereoisomerism; D013729:Terpenes / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D013729:Terpenes; C000604291:rhodonoid A; C000604292:rhodonoid B