Total synthesis of (+)-yohimbine via an enantioselective organocatalytic Pictet-Spengler reaction.
J Org Chem
; 76(21): 8907-12, 2011 Nov 04.
Article
en En
| MEDLINE
| ID: mdl-21950549
The binolphosphoric acid-catalyzed Pictet-Spengler reaction of an N-(5-oxy-2,4-pentadienyl)tryptamine derivative with methyl 5-oxo-2-(phenylseleno)pentanoate leads to the tetrahydro-ß-carboline in a 92:8 enantiomeric ratio. This product is easily converted into the substrate for a stereoselective intramolecular Diels-Alder reaction of the type earlier reported by Jacobsen. These two key steps constitute the basis for a nine-step total synthesis of (+)-yohimbine from tryptamine. A similar asymmetric Pictet-Spengler reaction was applied to the synthesis of an intermediate in the recent total synthesis of corynantheidine by Sato.
Texto completo:
1
Colección:
01-internacional
Base de datos:
MEDLINE
Asunto principal:
Yohimbina
/
Triptaminas
Idioma:
En
Revista:
J Org Chem
Año:
2011
Tipo del documento:
Article
País de afiliación:
Países Bajos
Pais de publicación:
Estados Unidos