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Volumn 61, Issue 10, 1996, Pages 3398-3405

Practical route to a new class of LTD4 receptor antagonists

Author keywords

[No Author keywords available]

Indexed keywords

L 691698; L 699392; LEUKOTRIENE D4 RECEPTOR; LEUKOTRIENE RECEPTOR BLOCKING AGENT; UNCLASSIFIED DRUG;

EID: 15844376844     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo952103j     Document Type: Article
Times cited : (252)

References (48)
  • 4
    • 0026736070 scopus 로고
    • and references cited therein
    • (d) Musser, J. H.; Kreft, A. F. J. Med. Chem. 1992, 35, 2501 and references cited therein.
    • (1992) J. Med. Chem. , vol.35 , pp. 2501
    • Musser, J.H.1    Kreft, A.F.2
  • 7
    • 0024370815 scopus 로고
    • McNamara, J. M.; Leazer, J. L.; Bhupathy, M.; Amato, J. S.; Reamer, R. A.; Reider, P. J.; Grabowski, E. J. J. J. Org. Chem. 1989, 54, 3718. For the preparation of the chiral derivative (MK-0679) by lipase-catalyzed asymmetric hydrolysis, see: Hughes, D. L.; Bergan, J. J., Amato, J. S.; Bhupathy, M.; Leazer, J. L.; McNamara, J. M.; Sidler, D. R.; Reider, P. J.; Grabowski, E. J. J. J. Org Chem. 1990, 55, 6252.
    • (1989) J. Org. Chem. , vol.54 , pp. 3718
    • McNamara, J.M.1    Leazer, J.L.2    Bhupathy, M.3    Amato, J.S.4    Reamer, R.A.5    Reider, P.J.6    Grabowski, E.J.J.7
  • 34
    • 0000303395 scopus 로고
    • For a list of other benzaldehyde-related ortho directing groups see ref 8
    • Directed ortho metalation of the cyclohexylimine of 4-chlorobenzaldehdye only provided BuLi attack at the imine and no detectable ortho lithiation. Ortho lithiation of the cyclohexylimines is reported to work only with aryl groups with electron-donating groups present; see: Ziegler, F. E.; Fowler, K. W. J. Org. Chem. 1976, 41, 1564. For a list of other benzaldehyde-related ortho directing groups see ref 8.
    • (1976) J. Org. Chem. , vol.41 , pp. 1564
    • Ziegler, F.E.1    Fowler, K.W.2
  • 35
    • 15844419574 scopus 로고    scopus 로고
    • note
    • Since the dimethylamide was ultimately desired, the metalation-carboxylation of 4-chlorobenzaldehyde was carried out with dimethylcarbamoyl chloride. The dimethylcarbamide derivative was obtained cleanly; however, upon subjecting the material to the coupling reaction the amide was easily hydrolyzed in situ to provide only 7b. (Equation Presented)
  • 44
    • 15844376511 scopus 로고    scopus 로고
    • note
    • The alkylation of the hydroxy ester 3b gave the crystalline product i. However, a major byproduct in the alkylation was the lactone ii (38%) formed by intramolecular esterification. Although the mixture of i and ii could be converted to 13, purification and isolation of the reaction intermediate was compromised. (Equation Presented)
  • 47
    • 0000633011 scopus 로고
    • Vinyl Substitutions with Organopalladium Intermediates
    • Trost, B. M., Ed.; Pergamon Press: New York, Chapter 3, (c) References cited in ref 5
    • (b) Heck, R. F. Vinyl Substitutions with Organopalladium Intermediates. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: New York, 1991; Vol. 4, Chapter 3, p 833. (c) References cited in ref 5.
    • (1991) Comprehensive Organic Synthesis , vol.4 , pp. 833
    • Heck, R.F.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.