Synthesis of docetaxel and butitaxel analogues through kinetic resolution of racemic beta-lactams with 7-O-triethylsilylbaccatin III.
J Org Chem
; 72(3): 756-9, 2007 Feb 02.
Article
em En
| MEDLINE
| ID: mdl-17253791
ABSTRACT
The kinetic resolution of racemic cis-4-phenyl- and cis-4-tert-butyl-3-hydroxy-beta-lactam derivatives with 7-O-triethylsilylbaccatin III yielded paclitaxel and butitaxel analogues with high diastereoselectivity. The results demonstrated that the tert-butyldimethylsilyl protecting group at the C3-hydroxy group of the beta-lactams provided optimum kinetic resolution in comparison with the sterically less demanding triethylsilyl group and the larger triisopropylsilyl group. In addition, it was found that the C4 beta-lactam substituents also influenced diastereoselectivity. The C4 tert-butyl-beta-lactams provided better diastereoselectivity than the corresponding C4 phenyl beta-lactams.
Texto completo:
1
Coleções:
01-internacional
Base de dados:
MEDLINE
Assunto principal:
Taxoides
/
Beta-Lactamas
/
Alcaloides
/
Antineoplásicos
Idioma:
En
Revista:
J Org Chem
Ano de publicação:
2007
Tipo de documento:
Article
País de afiliação:
Estados Unidos