Synthesis of (-)-epi-indolactam V by an intramolecular Buchwald-Hartwig C-N coupling cyclization reaction.
J Org Chem
; 78(15): 7727-34, 2013 Aug 02.
Article
em En
| MEDLINE
| ID: mdl-23845025
ABSTRACT
The synthetic efforts toward the concise synthesis of (-)-indolactam V from simple and commercially available starting materials using palladium- and copper-catalyzed intramolecular N-arylation strategy for the elaboration of the requisite nine-membered lactam ring as the key step are described. The incorporation of a turn-inducing structural element along the linear precursor was fundamental to achieve the heterocyclization step as well as obtain the correct regio- and chemoselectivity. The stereoselective nature in the C-N coupling cyclization reaction is interpreted in terms of minimization of allylic strain at the transition state for the palladium-amido complex formation. Meanwhile, the synthesis of the (-)-epi-indolactam V and its enantiomer have been accomplished.
Texto completo:
1
Coleções:
01-internacional
Base de dados:
MEDLINE
Assunto principal:
Indóis
/
Lactamas
Idioma:
En
Revista:
J Org Chem
Ano de publicação:
2013
Tipo de documento:
Article
País de afiliação:
Itália