A PRACTICAL SYNTHESIS OF THE ANTITUMOR AGENT 2-METHYL-4-DEOXYISOPICROPODOPHYLLOTOXIN AND RELATED PODOPHYLLIN ANALOGS

被引：9

作者：

BEARD, AR ^{[1
]}

HAZELL, SJ ^{[1
]}

MANN, J ^{[1
]}

PALMER, C ^{[1
]}

机构：

[1] UNIV READING,DEPT CHEM,READING RG6 2AD,BERKS,ENGLAND

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1993年 / 11期

关键词：

D O I：

10.1039/p19930001235

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We describe an efficient, six-stage synthesis of 2-methyl-4-deoxyisopicropodophyllotoxin, which proceeds via a Diels-Alder cycloaddition between 2-methylmaleic anhydride and the orthoquinodimethane generated by treatment of 5-[1-acetoxy-1-(3',4',5'-trimethoxyphenyl)methyl]-6-trimethyl-silylmethyl-1,3-benzodioxole with silica gel at 60-degrees-C. The podophyllin was converted into a number of 4'-ester derivatives. This procedure was also used to prepare a diazapodophyllin via the use of 4-phenyl-1,2,4-triazoline-3,5-dione as dienophile.

引用

页码：1235 / 1238

页数：4

共 13 条

[1] MECHANICAL ACTIVATION OF MAGNESIUM TURNINGS FOR THE PREPARATION OF REACTIVE GRIGNARD-REAGENTS [J].