A novel one-pot approach of hexahydropyrrolo[2,3-b]indole nucleus by a cascade addition/cyclization strategy: synthesis of (+/-)-esermethole.
A practical and efficient synthesis of 3-substituted hexahydropyrrolo[2,3-b]indole is described. The addition/cyclization of 3-substituted indoles with alpha,beta-dehydroamino esters in the presence of a Lewis acid provides hexahydropyrrolo[2,3-b]indole adducts in good yields and stereoselectivities. This approach has been applied to the concise synthesis of esermethole employing an appropriately substituted indole and an N-acyl dehydroamino ester.
Lucarini
Simone
S
Department of Drug and Health Sciences, University of Urbino Carlo Bo, Piazza del Rinascimento 6, 61029 Urbino (PU), Italy.
Bartoccini
Francesca
F
Battistoni
Flavia
F
Diamantini
Giuseppe
G
Piersanti
Giovanni
G
Righi
Marika
M
Spadoni
Gilberto
G
D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D003500:Cyclization; D007211:Indoles / Q000138:chemical synthesis / Q000737:chemistry*; D058116:Lewis Acids / Q000737:chemistry; D010830:Physostigmine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D011758:Pyrroles / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D000470:Alkaloids; D007211:Indoles; D058116:Lewis Acids; D011758:Pyrroles; C518152:esermethole; D010830:Physostigmine