Fluorination of betulinines and other triterpenoids with DAST

被引：18

作者：

Biedermann, D

Sarek, J

Klinot, J

Hajduch, M

Dzubak, P

机构：

[1] Charles Univ Prague, Fac Sci, Dept Organ & Nucl Chem, Prague 12843 2, Czech Republic

[2] Palacky Univ, Fac Med, Dept Pediat, Expt Med Lab, Olomouc 77520, Czech Republic

来源：

SYNTHESIS-STUTTGART | 2005年 / 07期

关键词：

antitumor agents; fluorine; rearrangements; steric hindrance; terpenoids;

D O I：

10.1055/s-2005-861861

中图分类号：

O62 [有机化学];

学科分类号：

070303 [有机化学]; 081704 [应用化学];

摘要：

Betulinines are lupane, des-E-lupane, 18-lupene, 20(29)-lupene and 18 alpha-oleanane derivatives with antitumor activity. We examined fluorination of these derivatives using diethylammosulfur trifluoride (DAST) as fluorinating agent. We prepared 19 beta,28-epoxy-2,2-difluoro- 18 alpha-oleanan-3-one (3c), 19 beta,28-epoxy-2,2-difluoro-18 alpha-oleanan-3 beta-ol (4a), methyl 3 beta-acetoxy-30-fluorolup-20(29)-ene-28-oate (6b), 3 beta,28-diacetoxy-22-oxo-21,21-difluorolup-18-ene (8b) and several other fluorinated betulinines for in vitro cytotoxicity tests which failed to demonstrate significant anticancer activity so far.

引用

页码：1157 / 1163

页数：7

共 22 条

[1]

SYNTHESIS OF ALPHA,ALPHA-DIFLUORONITRILES FROM ACYL CYANIDES [J].