Enantioselective total synthesis of the indole alkaloid 16-episilicine.
The first total synthesis of (-)-16-episilicine has been completed from a phenylglycinol-derived bicyclic lactam, the key steps being stereoselective conjugate addition and alkylation reactions, and a ring-closing metathesis.
Amat
Mercedes
M
Laboratory of Organic Chemistry, Faculty of Pharmacy, and Institute of Biomedicine (IBUB), University of Barcelona, Barcelona, Spain. amat@ub.edu
Checa
Begoña
B
Llor
Núria
N
Molins
Elies
E
Bosch
Joan
J
D000478:Alkylation; D003500:Cyclization; D004983:Ethanolamines; D005998:Glycine / Q000031:analogs & derivatives / Q000138:chemical synthesis / Q000737:chemistry; D026121:Indole Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D007769:Lactams / Q000138:chemical synthesis / Q000737:chemistry*; D010881:Piperidones / Q000138:chemical synthesis / Q000737:chemistry; D013237:Stereoisomerism
D004983:Ethanolamines; D026121:Indole Alkaloids; D007769:Lactams; D010881:Piperidones; C542151:silicine; C005332:N-phenylethanolamine; D005998:Glycine