First enantiocontrolled formal synthesis of (+)-neovibsanin B, a neurotrophic diterpenoid.
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.
Esumi
Tomoyuki
T
Faculty of Pharmaceutical Sciences, Tokushima Bunri University, Yamashiro-cho, Tokushima 770-8514, Japan.
Mori
Takehiro
T
Zhao
Ming
M
Toyota
Masao
M
Fukuyama
Yoshiyasu
Y
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
D004224:Diterpenes; D009414:Nerve Growth Factors; C539540:neovibsanin A