Total synthesis of (+)-epiquinamide.
The stereoselective total synthesis of the novel quinolizidine alkaloid (+)-epiquinamide is presented, starting from the amino acid l-allysine ethylene acetal. Key steps in the synthesis involved a highly diastereoselective N-acyliminium ion allylation and a ring-closing metathesis reaction to provide the bicyclic skeleton. [reaction: see text]
Wijdeven
Marloes A
MA
Chiralix B.V., P.O. Box 31070, 6503 CB Nijmegen, The Netherlands, Radboud University Nijmegen, IMM, Toernooiveld 1, 6525 ED Nijmegen, The Netherlands.
Botman
Peter N M
PN
Wijtmans
Roel
R
Schoemaker
Hans E
HE
Rutjes
Floris P J T
FP
Blaauw
Richard H
RH
D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D003500:Cyclization; D008968:Molecular Conformation; D015394:Molecular Structure; D011807:Quinolizines / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D000470:Alkaloids; D011807:Quinolizines; C481035:epiquinamide