Enantioselective formal synthesis of ent-rhynchophylline and ent-isorhynchophylline.
Starting from (S)-tryptophanol, a formal synthesis of ent-rhynchophylline and ent-isorhynchophylline, involving stereoselective cyclocondensation, spirocyclization, and alkylation reactions, and the final adjustment of the oxidation level at the oxindole and piperidine moieties, is reported.
Laboratory of Organic Chemistry, Faculty of Pharmacy, Institute of Biomedicine (IBUB), University of Barcelona, 08028-Barcelona, Spain. amat@ub.edu
Mercedes
M
Amat
Carlos
C
Ramos
Maria
M
Pérez
Elies
E
Molins
Pedro
P
Florindo
Maria M M
MM
Santos
Joan
J
Bosch
D001688:Biological Products / Q000737:chemistry; D060326:Chemistry Techniques, Synthetic; D026121:Indole Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry*; D000078183:Oxindoles; D013237:Stereoisomerism; D013379:Substrate Specificity; D014363:Tryptamines / Q000737:chemistry; D014364:Tryptophan / Q000031:analogs & derivatives / Q000737:chemistry
D001688:Biological Products; D026121:Indole Alkaloids; D000078183:Oxindoles; D014363:Tryptamines; C030820:tryptamine; C052714:rhyncophylline; C069544:tryptophanol; D014364:Tryptophan