title: Stereocontrolled Total Syntheses of (-)-Rotenone and (-)-Dalpanol by 1,2-Rearrangement and SNAr Oxycyclizations.
abstract: The total syntheses of (-)-rotenone and (-)-dalpanol have been achieved by a group-selective, stereospecific 1,2-shift of an epoxy alcohol and SNAr cyclizations. Three oxacycles are constructed, thus illustrating a versatile synthetic route to various rotenoids.
authors.affiliation: Department of Chemistry, Tokyo Institute of Technology, 2-12-1 O-okayama, Meguro-ku, Tokyo, 152-8551, Japan.
authors.forename: Kayo
authors.initials: K
authors.lastname: Nakamura
authors.affiliation: Department of Chemistry, Tokyo Institute of Technology, 2-12-1 O-okayama, Meguro-ku, Tokyo, 152-8551, Japan.
authors.forename: Ken
authors.initials: K
authors.lastname: Ohmori
authors.affiliation: Department of Chemistry, Tokyo Institute of Technology, 2-12-1 O-okayama, Meguro-ku, Tokyo, 152-8551, Japan.
authors.forename: Keisuke
authors.initials: K
authors.lastname: Suzuki
mesh_terms: D001688:Biological Products / Q000138:chemical synthesis* / Q000737:chemistry; D060326:Chemistry Techniques, Synthetic / Q000379:methods; D003500:Cyclization; D029866:Derris / Q000737:chemistry; D006576:Heterocyclic Compounds, 4 or More Rings / Q000138:chemical synthesis* / Q000737:chemistry; D012402:Rotenone / Q000032:analysis / Q000138:chemical synthesis*; D013237:Stereoisomerism
chemical_list: D001688:Biological Products; D006576:Heterocyclic Compounds, 4 or More Rings; C000625483:dalpanol; D012402:Rotenone
keywords: cyclizations; heterocycles; natural products; rearrangements; total synthesis