title: Total syntheses of (Sp)-(+)- and (Rp)-(-)-spiniferin-1, a pair of unusual natural products with planar chirality.
abstract: (S(p))-(+)-Spiniferin-1 and (R(p))-(-)-spiniferin-1, a pair of unusual marine natural products with planar chirality, were firstly synthesized via a polyfluoroalkanosulfonyl fluoride induced homoallylic carbocation rearrangement reaction. The chiral resolution and palladium-catalyzed β-H elimination of allylic alcohol derivatives were considered as the key steps of these divergent syntheses.
authors.affiliation: Key Laboratory of Synthetic Chemistry of Natural Substances, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai, China.
authors.forename: Yun-Shan
authors.initials: YS
authors.lastname: Sun
authors.forename: Kai
authors.initials: K
authors.lastname: Ding
authors.forename: Wei-Sheng
authors.initials: WS
authors.lastname: Tian
mesh_terms: D000475:Alkenes / Q000737:chemistry; D001688:Biological Products / Q000138:chemical synthesis* / Q000737:chemistry*; D006575:Heterocyclic Compounds, 3-Ring / Q000138:chemical synthesis* / Q000737:chemistry*; D011108:Polymers / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000475:Alkenes; D001688:Biological Products; D006575:Heterocyclic Compounds, 3-Ring; D011108:Polymers; C558605:spiniferin-1