Total synthesis of tetrahydrolipstatin and stereoisomers via a highly regio- and diastereoselective carbonylation of epoxyhomoallylic alcohols.
J Am Chem Soc
; 136(30): 10814-20, 2014 Jul 30.
Article
em En
| MEDLINE
| ID: mdl-25004122
ABSTRACT
A concise enantioselective synthesis of tetrahydrolipstatin (THL) and seven stereoisomers has been achieved. The synthesis of THL was accomplished in 10 steps and 31% overall yield from an achiral ynone. Key to the success of the approach is the use of a bimetallic [Lewis acid](+)[Co(CO)4](-) catalyst for a late-stage regioselective carbonylation of an enantiomerically pure cis-epoxide to a trans-ß-lactone. The success of this route to THL and its stereoisomers also demonstrated the practicality of the carbonylation catalyst for complex molecule synthesis as well as its functional group compatibility.
Texto completo:
1
Bases de dados:
MEDLINE
Assunto principal:
Fármacos Antiobesidade
/
Propanóis
/
Inibidores Enzimáticos
/
Compostos de Epóxi
/
Lactonas
Idioma:
En
Revista:
J Am Chem Soc
Ano de publicação:
2014
Tipo de documento:
Article
País de afiliação:
Estados Unidos