A synthetic approach to ervatamine-silicine alkaloids. Enantioselective total synthesis of (-)-16-episilicine.
Starting from an appropriate unsaturated phenylglycinol-derived oxazolopiperidone lactam, the synthesis of (-)-16-episilicine is reported, the key steps being a stereoselective conjugate addition, a stereoselective alkylation, and a ring-closing metathesis reaction. This represents the first enantioselective total synthesis of an alkaloid of the silicine group.
Amat
Mercedes
M
Laboratory of Organic Chemistry, Faculty of Pharmacy, and Institute of Biomedicine, University of Barcelona, 08028 Barcelona, Spain. amat@ub.edu
Llor
Núria
N
Checa
Begoña
B
Molins
Elies
E
Bosch
Joan
J
D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry*; D002384:Catalysis; D000075202:Contraindications; D018360:Crystallography, X-Ray; D026121:Indole Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry*; D007769:Lactams / Q000737:chemistry*; D015394:Molecular Structure; D046948:Secologanin Tryptamine Alkaloids
D000470:Alkaloids; D026121:Indole Alkaloids; D007769:Lactams; D046948:Secologanin Tryptamine Alkaloids; C542151:silicine; C017291:ervatamine