Total Synthesis of Polycavernosides A and B, Two Lethal Toxins from Red Alga.
J Org Chem
; 82(24): 13204-13219, 2017 12 15.
Article
en En
| MEDLINE
| ID: mdl-29124933
ABSTRACT
Polycavernosides A and B are glycosidic macrolide natural products isolated as the toxins causing fatal human poisoning by the edible red alga Gracilaria edulis (Polycavernosa tsudai). Total synthesis of polycavernosides A and B has been achieved via a convergent approach. The synthesis of the macrolactone core structure is highlighted by the catalytic asymmetric syntheses of the two key fragments using hetero-Diels-Alder reaction and Kiyooka aldol reaction as the key steps, their union through Suzuki-Miyaura coupling, and Keck macrolactonization. Finally, glycosylation with the l-fucosyl-d-xylose unit and construction of the polyene side chain through Stille coupling completed the total synthesis of polycavernosides A and B.
Texto completo:
1
Banco de datos:
MEDLINE
Asunto principal:
Toxinas Bacterianas
/
Macrólidos
/
Disacáridos
/
Rhodophyta
Idioma:
En
Revista:
J Org Chem
Año:
2017
Tipo del documento:
Article
País de afiliación:
Japón