title: Total synthesis of (R,R,R)-γ-tocopherol through Cu-catalyzed asymmetric 1,2-addition.
abstract: Based on the asymmetric copper-catalyzed 1,2-addition of Grignard reagents to ketones, (R,R,R)-γ-tocopherol has been synthesized in 36 % yield over 12 steps (longest linear sequence). The chiral center in the chroman ring was constructed with 73 % ee by the 1,2-addition of a phytol-derived Grignard reagent to an α-bromo enone prepared from 2,3-dimethylquinone.
authors.affiliation: Stratingh Institute for Chemistry, University of Groningen, Nijenborgh 7, 9747 AG, Groningen (The Netherlands).
authors.forename: Zhongtao
authors.initials: Z
authors.lastname: Wu
authors.forename: Syuzanna R
authors.initials: SR
authors.lastname: Harutyunyan
authors.forename: Adriaan J
authors.initials: AJ
authors.lastname: Minnaard
mesh_terms: D002384:Catalysis; D003300:Copper / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism; D024504:gamma-Tocopherol / Q000138:chemical synthesis*
chemical_list: D003300:Copper; D024504:gamma-Tocopherol
keywords: (R,R,R)-γ-tocopherol; 1,2-addition; asymmetric catalysis; natural product synthesis; vitamin E