Asymmetric synthesis of (-)-adaline.
[reaction: see text] An enantioselective total synthesis of (-)-adaline has been achieved starting from a chiral 6,6-disubstituted piperidone derivative previously prepared by diastereoselective allylation of a chiral tricyclic N-acyl-N,O-acetal. The key steps include lithium ion-activated SN2-type alkynylation of the tricyclic N,O-acetal leading to exclusive formation of the (6S)-ethynylpiperidine and ring-closing olefin metathesis of the (2R,6S)-cis-2,6-dialkenylpiperidine for constructing the bridged azabicyclononane.
Itoh
Toshimasa
T
School of Pharmacy, Tokyo University of Pharmacy and Life Science, 1432-1 Horinouchi, Hachioji, Tokyo 192-0392, Japan.
Yamazaki
Naoki
N
Kibayashi
Chihiro
C
D000470:Alkaloids / Q000138:chemical synthesis*; D000818:Animals; D001952:Bridged-Ring Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D001517:Coleoptera / Q000737:chemistry*; D010880:Piperidines / Q000138:chemical synthesis* / Q000737:chemistry; D010881:Piperidones / Q000737:chemistry; D013237:Stereoisomerism
D000470:Alkaloids; D001952:Bridged-Ring Compounds; D010880:Piperidines; D010881:Piperidones; C475960:adaline; C418568:adalinine