Convergent synthesis of (+)-carambolaflavone A, an antidiabetic agent using a bismuth triflate-catalyzed C-aryl glycosylation.
Org Biomol Chem
; 20(14): 2822-2830, 2022 04 06.
Article
em En
| MEDLINE
| ID: mdl-35156978
ABSTRACT
We describe a convergent total synthesis of carambolaflavone A, a natural flavonoid C-aryl glycoside with significant antihyperglycemic properties. The synthesis features a bismuth triflate-catalyzed stereoselective C-aryl glycosylation of a flavan derivative and an appropriately protected D-fucose derivative as the key step. Inexpensive and non-toxic bismuth triflate provided the best results among various other Lewis acids screened for this C-aryl glycosylation. The method can be utilized for the synthesis of other bioactive C-glycosyl flavonoids. The glycosylation partners were synthesized from commercially available (±)-naringenin and D-(+)-galactose, respectively. An oxidative bromination and elimination reaction sequence was utilized to construct the flavone. The natural product is obtained in 13 steps (longest linear sequence) from D-(+)-galactose.
Texto completo:
1
Base de dados:
MEDLINE
Assunto principal:
Galactose
/
Hipoglicemiantes
Idioma:
En
Revista:
Org Biomol Chem
Assunto da revista:
BIOQUIMICA
/
QUIMICA
Ano de publicação:
2022
Tipo de documento:
Article
País de afiliação:
Estados Unidos