Complementary asymmetric routes to (R)-2-(7-hydroxy-2,3-dihydro-1H-pyrrolo[1,2-a]indol-1-yl)acetate.
Org Lett
; 14(24): 6306-9, 2012 Dec 21.
Article
em En
| MEDLINE
| ID: mdl-23210718
ABSTRACT
Two distinct and scalable enantioselective approaches to the tricyclic indole (R)-2-(7-hydroxy-2,3-dihydro-1H-pyrrolo[1,2-a]indol-1-yl)acetate, an important synthon for a preclinical S1P(1) receptor agonist, are reported. Route 1 employs a modified version of Smith's modular 2-substituted indole synthesis as the key transformation. Route 2 involves a highly enantioselective CuH-catalyzed 1,4-hydrosilylation as the stereodefining step. Both routes can be performed without chromatography to provide multigram quantities of the tricycle in ≥98% ee.
Texto completo:
1
Base de dados:
MEDLINE
Assunto principal:
Pirróis
/
Indóis
/
Acetatos
Idioma:
En
Ano de publicação:
2012
Tipo de documento:
Article