Asymmetric Synthesis of (l′R,3R,4R)-4-acetoxy-3-(l′-((tert-butyldimethylsilyl)oxy)ethyl)-2-azetidinone and Other 3-(r-hydroxyethyl)-2-azetidinones from (£)-(+)-ethyl 3-hydroxybutanoate: Formal Total Synthesis of (+)-thienamycin

Journal of the American Chemical Society

Volumn 109, Issue 4, 1987, Pages 1129-1135

  Georg, Gunda I ^a   Kant, Joydeep ^a   Gill, Harpal S ^a  

^a UNIVERSITY OF KANSAS   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

3 (1 HYDROXYETHYL) 2 AZETIDINONE DERIVATIVE; THIENAMYCIN; UNCLASSIFIED DRUG;

DRUG ANALYSIS; DRUG IDENTIFICATION; DRUG STRUCTURE; DRUG SYNTHESIS; INFRARED SPECTROPHOTOMETRY; METHODOLOGY; NONHUMAN; NUCLEAR MAGNETIC RESONANCE; PRIORITY JOURNAL; THEORETICAL STUDY;

EID: 0023149442     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00238a023     Document Type: Article

References (28)

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21. Anti elimination of (8£,6S)-configurated 3-(hydroxyethyl)azetidinones is expected to produce Z-configurated enelactams. Because of ambiguous chemical shifts, we confirmed the structure of 25 according to a protocol (eq 3) reported by Merck. Johnston, D. B. R.; Schmitt, S. M.; Bouffard, F. A.; Christensen, B. G. J. Am. Chem. Soc. 1978, 100, 313.
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