Novel asymmetric approach to proline-derived spiro-β-lactams

Journal of Organic Chemistry

Volumn 69, Issue 17, 2004, Pages 5766-5769

  Khasanov, Alisher B ^a   Ramirez Weinhouse, Michele M ^b   Webb, Thomas R ^a   Thiruvazhi, Mohan ^a  

^a ChemBridge Research Laboratories   (United States)

^b PFIZER GLOBAL RESEARCH AND DEVELOPMENT   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACIDS; CHEMICAL REACTIONS; SYNTHESIS (CHEMICAL);

CHIRALS; STAUDINGER CHEMISTRY; STEREOSELECTIVITY;

ORGANIC COMPOUNDS;

BETA LACTAM; CHLORIDE; IMINE; PROLINE; SULFONYLOXYPROLINE; UNCLASSIFIED DRUG;

ARTICLE; ASYMMETRIC SYNTHESIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHEMISTRY; CHIRALITY; DIASTEREOISOMER; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; OPTICAL ROTATION; STAUDINGER CHEMISTRY; STEREOCHEMISTRY; THIN LAYER CHROMATOGRAPHY;

BETA-LACTAMS; CATALYSIS; CHEMISTRY, ORGANIC; IMINES; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR STRUCTURE; PROLINE; STEREOISOMERISM;

EID: 4043181084     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo049430o     Document Type: Article

References (26)

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10. This work was presented at 225th National Meeting of the American Chemical Society, New Orleans, LA, 2003; Abstract ORGN 452.
11. The "R" and "S" configurations at the spiranic carbon of spirolactam induce different conformations when incorporated in a peptide: (a) Brown, J. R.; Clegg, S. P.; Ewan, G. B.; Hagan, R. M.; Ireland, S. J.; Jordan, C. C.; Porter, B.; Ross, B. C.; Ward, P. In Molecular Recognition: Chemical and Biochemical Problems; Roberts, S. M., Ed.; Royal Society of Chemistry Special Publication No. 78; Royal Society of Chemistry: Lechtworth, 1989; pp 94-111.
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24. The alkene protons of 10 resonate at 6.07 and 5.83 ppm suggesting that the double bond is between C-7 and C-8; see: Donohoe, T. J.; House D. J. Org. Chem. 2002, 67, 5015-5018. Lack of signals at about 7.0 ppm precludes the possibility of a C-6, C-7 double bond in 10; see: Oliveira, D. F.; Miranda, P. C. M. L.; Correia, C. R. D. J. Org. Chem. 1999, 64, 6646-6652. In any event, the position of the double bond was immaterial to the outcome of the project.
25. The alkene protons of 10 resonate at 6.07 and 5.83 ppm suggesting that the double bond is between C-7 and C-8; see: Donohoe, T. J.; House D. J. Org. Chem. 2002, 67, 5015-5018. Lack of signals at about 7.0 ppm precludes the possibility of a C-6, C-7 double bond in 10; see: Oliveira, D. F.; Miranda, P. C. M. L.; Correia, C. R. D. J. Org. Chem. 1999, 64, 6646-6652. In any event, the position of the double bond was immaterial to the outcome of the project.
26. Lactam nitrogen of racemic 14 was deprotected using CAN in 30% unoptimized yield to afford the azetidinone 15. Further application of azetidinones such as 15 in optically active form toward synthesis of novel β-turns will be reported in due course: Siegel, D.; Khasanov, A.; Thiruvazhi, M. Unpublished results.