Stereoselective synthesis of fluorine-containing analogues of anti-bacterial sanfetrinem and LK-157

被引：30

作者：

Mohar, Barbara ^{[1
]}

Stephan, Michel ^{[1
]}

Urleb, Uros ^{[2
]}

机构：

[1] Natl Inst Chem, Lab Organ & Med Chem, Ljubljana 1001, Slovenia

[2] Lek Pharmaceut Dd, Ljubljana 1526, Slovenia

来源：

TETRAHEDRON | 2010年 / 66卷 / 23期

关键词：

beta-Lactam; Asymmetric transfer hydrogenation; Ruthenium; Total synthesis; ENANTIOSELECTIVE TRANSFER HYDROGENATION; RUTHENIUM-CATALYZED OXIDATION; BETA-LACTAM ANTIBIOTICS; KEY INTERMEDIATE; CARBONYL; TRINEMS; LIGANDS; PENEMS; ESTERS;

D O I：

10.1016/j.tet.2010.03.104

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The synthesis of (1'S,3R,4R)-4-acetoxy-3-(1'-trimethylsilyloxy-2',2',2'-trifluoroethyl)-2-azetidinone (10) precursor of modified carbapenems is described relying upon [Ru(C6Me6)(S,S)-(CH2)(5)NSO2DPEN]-catalyzed asymmetric transfer hydrogenation under dynamic kinetic resolution using HCO2H-Et3N. This fluorine-containing precursor yielded the targeted trinems 1 and 2 via a stereoselective key step condensation with lithium (S)-6-methoxy-cyclohexenolate. (C) 2010 Elsevier Ltd. All rights reserved.

引用

页码：4144 / 4149

页数：6