Ring-expansion protocol: preparation of synthetically versatile dihydrotropones.
J Org Chem
; 74(2): 917-20, 2009 Jan 16.
Article
en En
| MEDLINE
| ID: mdl-19053605
ABSTRACT
A ring-expansion protocol that consisted of the 1,2-addition of various enolate nucleophiles to 6-trimethylsiloxy-2-cyclohexene-1-one (1) and the NaIO(4)-promoted oxidative ring opening of the resulting diols 2, followed by an intramolecular Knoevenagel condensation, furnished versatile dihydrotropones 6. Maintaining Z-configuration in the oxidative ring-opening products 3 is crucial for the success of the ring-expansion strategy. Dihydrotropones 6 are ripe for further elaborations such as oxidation to tropones 8 and Diels-Alder reaction with the Danishefsky's diene 10 to afford polycyclic compounds 12.
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1
Bases de datos:
MEDLINE
Asunto principal:
Tropolona
Idioma:
En
Revista:
J Org Chem
Año:
2009
Tipo del documento:
Article