Enantioselective synthesis of 12-amino alkylidenecyclopentenone prostaglandins.
J Org Chem
; 67(13): 4399-406, 2002 Jun 28.
Article
em En
| MEDLINE
| ID: mdl-12076134
ABSTRACT
An enantioselective synthesis of new 12-amino alkylidenecyclopentenone prostaglandins is reported. The key step of the synthesis involved a [3.3] sigmatropic rearrangement of an asymmetric allylic cyanate to elaborate an asymmetric 5-amino-1,6-diene which was further transformed into cyclopentenone by successive ring-closing metathesis reaction catalyzed by the Grubbs reagent and one-pot oxidation. A palladium-catalyzed cross-coupling reaction on a 5-iodo-1,5-diene allowed the synthesis of prostanoids with variable Rw side chains. These new compounds exhibit high cytotoxic activities.
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Base de dados:
MEDLINE
Assunto principal:
Prostaglandinas A
/
Prostaglandinas A Sintéticas
Limite:
Animals
Idioma:
En
Revista:
J Org Chem
Ano de publicação:
2002
Tipo de documento:
Article
País de afiliação:
França