A concise synthetic route to the stereotetrad core of the briarane diterpenoids.
Org Lett
; 17(9): 2218-21, 2015 May 01.
Article
em En
| MEDLINE
| ID: mdl-25871809
ABSTRACT
A concise synthesis (under 10 steps) of the stereotetrad core of the briarane diterpenoids is reported. This approach harnesses the unique reactivity of salicylate ester derived 2,5-cyclohexadienones to quickly build complexity. In particular, a highly diastereoselective acetylide conjugate addition/ß-ketoester alkylation sequence was used to set the relative configuration of the C1 (quaternary) and C10 (tertiary) vicinal stereocenters. The sterochemical outcome of the ß-ketoester alkylation appears to be governed by torsional steering in the transition state.
Texto completo:
1
Base de dados:
MEDLINE
Assunto principal:
Diterpenos
/
Cicloexenos
Idioma:
En
Ano de publicação:
2015
Tipo de documento:
Article