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
收藏
页码：4144 / 4149
页数：6
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