Cascade cyclization triggered by imine formation. Formal synthesis of the alkaloid (±)-stemoamide and its 9a-epimer

A concise formal synthesis of stemoamide ( 1) and its 9a-epimer 14in 5 steps is described featuring a cas-cade cyclization triggered by imine formation. A good selectivity for either epimer is readily accom-plished by variation of the ester ( 9bor 9a, respectively) and the reaction conditions.

Detalhes bibliográficos
Autores: Brito, Gilmar A., Sarotti, Ariel Marcelo, Wipf, Peter, Pilli, Ronaldo A.
Formato: artículo
Estado:Versión publicada
Fecha de publicación:2015
País:Argentina
Recursos:Consejo Nacional de Investigaciones Científicas y Técnicas
Repositorio:CONICET Digital (CONICET)
Idioma:inglés
OAI Identifier:oai:ri.conicet.gov.ar:11336/5987
Acesso em linha:http://hdl.handle.net/11336/5987
Access Level:acceso abierto
Palavra-chave:Cascade Cyclization
Imine
Formal Synthesis
Stemoamide
https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
Descrição
Resumo:A concise formal synthesis of stemoamide ( 1) and its 9a-epimer 14in 5 steps is described featuring a cas-cade cyclization triggered by imine formation. A good selectivity for either epimer is readily accom-plished by variation of the ester ( 9bor 9a, respectively) and the reaction conditions.