Ladder polyether synthesis via epoxide-opening cascades directed by a disappearing trimethylsilyl group.
J Org Chem
; 75(8): 2681-701, 2010 Apr 16.
Article
em En
| MEDLINE
| ID: mdl-20302314
ABSTRACT
Epoxide-opening cascades offer the potential to construct complex polyether natural products expeditiously and in a manner that emulates the biogenesis proposed for these compounds. Herein we provide a full account of our development of a strategy that addresses several important challenges of such cascades. The centerpiece of the method is a trimethylsilyl (SiMe(3)) group that serves several purposes and leaves no trace of itself by the time the cascade has come to an end. The main function of the SiMe(3) group is to dictate the regioselectivity of epoxide opening. This strategy is the only general method of effecting endo-selective cascades under basic conditions.
Texto completo:
1
Coleções:
01-internacional
Base de dados:
MEDLINE
Assunto principal:
Polímeros
/
Silanos
/
Compostos de Epóxi
/
Éteres
Idioma:
En
Ano de publicação:
2010
Tipo de documento:
Article