Total synthesis of the postulated structure of fulicineroside.
Chemistry
; 19(23): 7423-36, 2013 Jun 03.
Article
en En
| MEDLINE
| ID: mdl-23576462
ABSTRACT
A total synthesis of the proposed structures of fulicineroside and its aglycone fulicinerine is reported. The tetrasubstituted dibenzofuran substructure was accessible either through a Pd-mediated ortho-metalation or by an Ir-catalyzed meta-borylation. The synthesis of the ß,ß,α-linked trisaccharide consisting of D-olivose, L-rhodinose, and L-rhamnose was challenged by the unprecedented ß-linked rhodinose. A Pd-catalyzed ß-selective glycosylation of a 4-epi-rhodinose and a subsequent Mitsunobu inversion provided selectively the ß-linked L-rhodinose-L-rhamnose disaccharide. Comparison with the reported data for the natural product and the aglycone suggests a misassignment of the structure of the natural product.
Texto completo:
1
Colección:
01-internacional
Banco de datos:
MEDLINE
Asunto principal:
Benzofuranos
/
Productos Biológicos
/
Desoxiazúcares
/
Disacáridos
/
Glicósidos
Idioma:
En
Revista:
Chemistry
Asunto de la revista:
QUIMICA
Año:
2013
Tipo del documento:
Article
País de afiliación:
Alemania