A novel one-pot approach of hexahydropyrrolo[2,3-b]indole nucleus by a cascade addition/cyclization strategy: synthesis of (+/-)-esermethole

Simone Lucarini; Francesca Bartoccini; Flavia Battistoni; Giuseppe Diamantini; Giovanni Piersanti; Marika Righi; Gilberto Spadoni

doi:10.1021/ol101527j

A novel one-pot approach of hexahydropyrrolo[2,3-b]indole nucleus by a cascade addition/cyclization strategy: synthesis of (+/-)-esermethole

Org Lett. 2010 Sep 3;12(17):3844-7. doi: 10.1021/ol101527j.

Authors

Simone Lucarini¹, Francesca Bartoccini, Flavia Battistoni, Giuseppe Diamantini, Giovanni Piersanti, Marika Righi, Gilberto Spadoni

Affiliation

¹ Department of Drug and Health Sciences, University of Urbino Carlo Bo, Piazza del Rinascimento 6, 61029 Urbino (PU), Italy.

PMID: 20795744
DOI: 10.1021/ol101527j

Abstract

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.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Alkaloids / chemical synthesis*
Alkaloids / chemistry
Catalysis
Combinatorial Chemistry Techniques
Cyclization
Indoles / chemical synthesis
Indoles / chemistry*
Lewis Acids / chemistry
Physostigmine / analogs & derivatives*
Physostigmine / chemical synthesis
Physostigmine / chemistry
Pyrroles / chemical synthesis*
Pyrroles / chemistry
Stereoisomerism

Substances

Alkaloids
Indoles
Lewis Acids
Pyrroles
esermethole
Physostigmine