title: First enantiocontrolled formal synthesis of (+)-neovibsanin B, a neurotrophic diterpenoid.
abstract: An enantiocontrolled formal synthesis of (+)-neovibsanin B has been achieved by a sequence that applies an asymmetric 1,4-addition of (H(2)C=CH)(2)Cu(CN)Li(2) to trisubstituted alpha,beta-carboxylic acid derivative 1 to induce the chirality at the C-11 all-carbon quaternary center. Together with a modified Negishi cyclic carbopalladation-carbonylative esterification tandem reaction for constructing the A-ring, the synthesis was completed.
authors.affiliation: Faculty of Pharmaceutical Sciences, Tokushima Bunri University, Yamashiro-cho, Tokushima 770-8514, Japan.
authors.forename: Tomoyuki
authors.initials: T
authors.lastname: Esumi
authors.forename: Takehiro
authors.initials: T
authors.lastname: Mori
authors.forename: Ming
authors.initials: M
authors.lastname: Zhao
authors.forename: Masao
authors.initials: M
authors.lastname: Toyota
authors.forename: Yoshiyasu
authors.initials: Y
authors.lastname: Fukuyama
mesh_terms: D002384:Catalysis; D003500:Cyclization; D004224:Diterpenes / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D015394:Molecular Structure; D009414:Nerve Growth Factors / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D013237:Stereoisomerism; D027925:Viburnum / Q000737:chemistry
chemical_list: D004224:Diterpenes; D009414:Nerve Growth Factors; C539540:neovibsanin A