Total synthesis of (+)-13-deoxytedanolide.
J Am Chem Soc
; 127(17): 6186-7, 2005 May 04.
Article
em En
| MEDLINE
| ID: mdl-15853320
ABSTRACT
A total synthesis of 13-deoxytedanolide is described. The synthesis features a highly stereoselective fragment assembly aldol reaction of methyl ketone 4 and aldehyde 5 to establish the complete carbon skeleton of the natural product in the form of aldol 15. The facile formation of the remarkably unreactive hemiketal 16 thwarted attempts to elaborate 15 to tedanolide. However, deoxygenation of the C(13)-hydroxyl of 16 provided the 13-deoxy hemiketal 17 that was smoothly elaborated to 13-deoxytedanolide.
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Coleções:
01-internacional
Base de dados:
MEDLINE
Assunto principal:
Macrolídeos
Limite:
Animals
Idioma:
En
Ano de publicação:
2005
Tipo de documento:
Article