STEROIDAL ALKENYLPHOSPHONATES VIA PALLADIUM-CATALYZED COUPLING REACTIONS

被引：10

作者：

SKODAFOLDES, R

KOLLAR, L

HORVATH, J

TUBA, Z

机构：

[1] UNIV VESZPREM,DEPT ORGAN CHEM,H-8200 VESZPREM,HUNGARY

[2] GEDEON RICHTER CHEM WORKS LTD,CHEM WORKS,BUDAPEST,HUNGARY

来源：

STEROIDS | 1995年 / 60卷 / 12期

基金：

美国国家科学基金会;

关键词：

COUPLING REACTION OF STEROIDS; STEROIDAL ALKENYLPHOSPHONATES; HOMOGENEOUS PALLADIUM(0) CATALYSTS;

D O I：

10.1016/0039-128X(95)00121-6

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

The palladium-catalyzed coupling of various 17-iodo-Delta(16) steroids (17-iodo-androst-16-ene, 17-iodo-4-methyl-4-aza-androst-16-en-3-one, and 17-iodo-4-aza-androst-16-en-3-one) with dialkyl phosphites (dimethyl phosphite, diethyl phosphite, and diisopropyl phosphite) was examined in detail. The only successful condition for homogeneous coupling involved carrying out the reaction in the absence of any solvents. A large excess of dialkyl phosphite was used, which means that the phosphite itself acted as a solvent. Eight new androst-16-ene derivatives with phosphonate groups at C-17 were synthesized and characterized. These steroids are of pharmacological interest as potential Sol-reductase inhibitors. Under the same conditions, methylation of lactam NH was observed using dimethyl phosphite.

引用

页码：791 / 795

页数：5

共 12 条

[1] EVIDENCE OF THE FORMATION OF ZEROVALENT PALLADIUM FROM PD(OAC)2 AND TRIPHENYLPHOSPHINE [J].