Enantio- and diastereo-controlled synthesis of (+)-juvabione employing organocatalytic desymmetrization and photoinduced fragmentation.
(+)-Juvabione, a natural sesquiterpene exhibiting insect juvenile hormone activity, has been synthesized from sigma-symmetric 4-(2-formyl-ethyl)cyclohexanone by employing organocatalytic asymmetric aldolization and Norrish I-type fragmentation as the key steps.
Itagaki
Noriaki
N
Graduate School of Pharmaceutical Sciences, Tohoku University, Aobayama, Sendai 980-8578, Japan.
Iwabuchi
Yoshiharu
Y
D002384:Catalysis; D003510:Cyclohexanes / Q000138:chemical synthesis*; D003512:Cyclohexanones / Q000737:chemistry*; D013237:Stereoisomerism
D003510:Cyclohexanes; D003512:Cyclohexanones; C414814:juvabione