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

• Published in: Tetrahedron Vol. 66; no. 23; pp. 4144 - 4149
• Main Authors: Mohar, Barbara, Stephan, Michel, Urleb, Uroš
• Format: Journal Article
• Language: English
• Published: Kidlington Elsevier Ltd 05-06-2010; Elsevier
• Subjects: Asymmetric transfer hydrogenation; Chemistry; Exact sciences and technology; Heterocyclic compounds; Heterocyclic compounds with only one n hetero atom and condensed derivatives; Organic chemistry; Preparations and properties; Ruthenium; Total synthesis; β-Lactam; PJLIYQFJRVPCJO-RVJQKOHUSA-N; Ruthenium; DKDWZKGCPZMFOF-ACLDMZEESA-N; BJLDXZKBNTYTLK-QWRGUYRKSA-N; β-Lactam; VFSJVWDGYZBAHH-VIFPVBQESA-N; RJPIMXLLAGIRCI-HRFVKAFMSA-N; Asymmetric transfer hydrogenation; Total synthesis; UZPGJFNHIDZDGN-BGDQHZHDSA-M; OAJNOWUAMHYMCY-HRFVKAFMSA-N; FVZXUCLYBAFEKN-AOSQYRGRSA-M; RWIBERNCNCZNOC-LNSPPBFMSA-N; QATCJSWHJOTVHO-UHFFFAOYSA-N; Catalytic reaction; Condensation reaction; Nitrogen heterocycle; β-Lactams; Lactam; Transition metal; Hydrogenation; Stereoselectivity; Carbapenem derivatives; Sanfetrinem; Lithium Organic compounds; Asymmetric synthesis; Optical resolution; Analog; Azetidine derivatives; Organic fluorine compounds; Antibacterial agent; Chemical synthesis; Platinoid; Ruthenium complex
• ISSN: 0040-4020; 1464-5416
• DOI: 10.1016/j.tet.2010.03.104

The synthesis of (1′
S,3
R,4
R)-4-acetoxy-3-(1′-trimethylsilyloxy-2′,2′,2′-trifluoroethyl)-2-azetidinone (
10) precursor of modified carbapenems is described relying upon [Ru(C
6Me
6)(
S,
S)–(CH
2)
5NSO
2DPEN]-catalyzed asymmetric transfer hydrogenation under dynamic kinetic resolution using HCO
2H–Et
3N. This fluorine-containing precursor yielded the targeted trinems
1 and
2 via a stereoselective key step condensation with lithium (
S)-6-methoxy-cyclohexenolate.
[Display omitted]