Total Synthesis of (+)-Furanomycin and Stereoisomers

Journal of the American Chemical Society

Volumn 102, Issue 25, 1980, Pages 7505-7510

  Semple, J Edward ^a   Wang, Pen C ^a   Lysenko, Zenon ^a   Joullié, Madeleine M ^a  

^a UNIVERSITY OF PENNSYLVANIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2 (2,5 DIHYDRO 5 METHYLFURYL)GLYCINE; DRUG ANALYSIS; DRUG IDENTIFICATION; DRUG STRUCTURE; DRUG SYNTHESIS; FURANOMYCIN; IN VITRO STUDY; INFRARED SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE; THEORETICAL STUDY;

EID: 0019186783     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00545a018     Document Type: Article

References (25)

1. A preliminary account of this work was presented at the 178th National Meeting of the American Chemical Society, Washington, D.C., September 1979, ORG 124,
2. The synthetic studies of the cis stereoisomers of furanomycin were taken in part from the Ph.D. dissertation of J. Edward Semple, University of Pennsylvania, 1980; the synthetic investigations of the trans stereoisomers of furanomycin were taken in part from the Ph.D. dissertation of Pen C. Wang, University of Pennsylvania, 1980.
3. Katagiri, K.; Tori, K.; Kimura, Y.; Yoshida, T.; Nagasaki, T.; Minato, H.J. Med. Chem. 1967, 10, 1149.
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8. Private communication from Professor M.J. Robins;
9. Ph.D. Dissertation of J.M. R. Parker, University of Alberta, 1980.
10. A recent communication from Dr. Katagiri has informed us of X-ray diffraction studies on furanomycin N-acetate, which revealed that the natural antibiotic does possess the (αS,2R,5S) configuration, thereby supporting our findings; J. Chem. Soc., Chem. Commun. 1980, 375.
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24. tert-Butyl isocyanide was prepared by a modification of the procedure of Ugi et al. (“Organic Syntheses“, Wiley: New York, 1973; Collect. Vol. V. p 300). Diphenyl ether was used instead of petroleum ether.
25. Prepared according to; Fieser, L.P.; Fieser, M. “Reagents for Organic Synthesis”; Wiley: New York, 1967; Vol. 1, p 729.