Synthesis of a transmembrane ionophore based on a C2-symmetric polyhydroxysteroid derivative

被引：16

作者：

Di Filippo, M

Izzo, I

Savignano, L

Tecilla, P

De Riccardis, F

机构：

[1] Univ Salerno, Dept Chem, I-84081 Baronissi, SA, Italy

[2] Univ Trieste, Dept Chem Sci, I-34127 Trieste, Italy

来源：

TETRAHEDRON | 2003年 / 59卷 / 10期

关键词：

polyhydroxysteroids; ionophores; ene reaction; amphiphiles;

D O I：

10.1016/S0040-4020(03)00108-X

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The synthesis of the C-2-symmetric bis-(20S)-5alpha-23,24-bisnorchol-16-en-3beta,6alpha,7beta-triol-22-terephthaloate (1), active as Na+-transporting transmembrane channel, has been achieved in 16 steps (10% overall yield) starting from the commercially available androst-5-en-3beta-ol-17-one (3). The straightforward stereospecific functionalization of the side-chain, via the 'ene' reaction, and the successful regioselective terephthaloylation of the C-22 hydroxy group, illustrate the efficiency of the synthetic strategy. (C) 2003 Elsevier Science Ltd. All rights reserved.

引用

页码：1711 / 1717

页数：7

共 52 条

[1] CONSIDERED AS REAGENTS AND SYNTHETIC METHODS .46. 1,8-DIAZABICYCLO[5.4.0]UNDEC-7-ENE(DBU) - AN EFFECTIVE BASE FOR THE INTRODUCTION OF TERT-BUTYLDIMETHYLSILYL GROUP IN ORGANIC-COMPOUNDS [J].