title: Construction of 3,6-anhydrohexosides via intramolecular cyclization of triflates and its application to the synthesis of natural product isolated from leaves of Sauropus rostratus.
abstract: A novel synthetic approach to construct various 3,6-anhydrohexosides via an intramolecular cyclization of corresponding triflates is described. The nucleophilic attack from C3 p-methoxybenzylated hydroxyl to C6 trifluoromethanesulfonate on triflate structures triggered the cyclization reaction to provide 3,6-anhydrohexosides in excellent yields, making the strategy more efficient with respect to the reported protocols. By applying this methodology, a concise first total synthesis of natural product isolated from leaves of Sauropus rostratus was accomplished.
authors.affiliation: State Key Laboratory of Natural Medicines and Department of Medicinal Chemistry, China Pharmaceutical University , Nanjing 210009, P. R. China.
authors.forename: Long
authors.initials: L
authors.lastname: Liu
authors.forename: Cheng-Qian
authors.initials: CQ
authors.lastname: Wang
authors.forename: Dan
authors.initials: D
authors.lastname: Liu
authors.forename: Wei-Gang
authors.initials: WG
authors.lastname: He
authors.forename: Jin-Yi
authors.initials: JY
authors.lastname: Xu
authors.forename: Ai-Jun
authors.initials: AJ
authors.lastname: Lin
authors.forename: He-Quan
authors.initials: HQ
authors.lastname: Yao
authors.forename: Genzoh
authors.initials: G
authors.lastname: Tanabe
authors.forename: Osamu
authors.initials: O
authors.lastname: Muraoka
authors.forename: Wei-Jia
authors.initials: WJ
authors.lastname: Xie
authors.forename: Xiao-Ming
authors.initials: XM
authors.lastname: Wu
mesh_terms: D001688:Biological Products / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D018360:Crystallography, X-Ray; D003500:Cyclization; D006027:Glycosides / Q000138:chemical synthesis* / Q000737:chemistry; D008968:Molecular Conformation; D015394:Molecular Structure; D029803:Phyllanthus / Q000737:chemistry*; D018515:Plant Leaves / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D001688:Biological Products; D006027:Glycosides