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Volumn 64, Issue 25, 1999, Pages 9282-9285

Formal asymmetric synthesis of a cholesterol absorption inhibitor bearing a 2-azaspiro[3.5]nonan-1-one Moiety

Author keywords

[No Author keywords available]

Indexed keywords

2 AZA 2 (4 FLUOROPHENYL) 8,11 DIOXA 3 [4 (BENZYLOXY)PHENYL]DISPIRO[3.2.4.2]TRIDECAN 1 ONE; AZETIDINONE DERIVATIVE; CHOLESTEROL; SCH 58053; UNCLASSIFIED DRUG;

EID: 0032761308     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo990933h     Document Type: Article
Times cited : (50)

References (37)
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    • 0029798970 scopus 로고    scopus 로고
    • Synthesis of spiro-fused azetidinone: (a) Wittig, G.; Hesse, A. Liebigs Ann. Chem. 1976, 500-510. (b) Spurr, P. R.; Hamon, D. P. G. J. Am. Chem. Soc. 1983, 105, 4734-4739. (c) Ikeda, M.; Uchino, T.; Ishibashi, H.; Tamura, Y.; Kido, M. J. Chem. Soc., Chem. Commun. 1984, 758-759. (d) Mullen, G. B.; Georgiev, V. S. Heterocycles 1986, 24, 3441-3446. (e) Ishibashi, H.; Nakamura, N.; Tatsunori, S.; Takeuchi, M.; Ikeda, M. Tetrahedron Lett. 1991, 32, 1725-1728. (f) Le Blanc, S.; Pete, J.-P.; Piva, O. Tetrahedron Lett. 1992, 33, 1993- 1996. (g) Fujisawa, T.; Ukaji, Y.; Noro, T.; Date, K.; Shimizu, M. Tetrahedron 1992, 48, 5629-5638. (h) Toda, F.; Miyamoto, H.; Takeda, K.; Matsugawa, R.; Maruyama, N. J. Org. Chem. 1993, 58, 6208-6211. (i) Chen, L.; Zaks, A.; Chacklamanil, S.; Dugar, S. J. Org. Chem. 1996, 61, 8341-8343.
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    • Chen, L.1    Zaks, A.2    Chacklamanil, S.3    Dugar, S.4
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    • 0032926147 scopus 로고    scopus 로고
    • After submission of our paper, a diastereo- and enantioselective synthesis of cholesterol absorption inhibitors has been reported. Wu, G.; Wong, Y.; Chen, X.; Ding, Z. J. Org. Chem. 1999, 64, 3714-3718.
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    • Wu, G.1    Wong, Y.2    Chen, X.3    Ding, Z.4
  • 30
    • 0344117742 scopus 로고    scopus 로고
    • The absolute configuration of 6 has not yet been determined
    • The absolute configuration of 6 has not yet been determined.
  • 31
    • 0344117743 scopus 로고    scopus 로고
    • Use of LDA did not exceed the selectivity obtained by use of LICA
    • Use of LDA did not exceed the selectivity obtained by use of LICA.
  • 32
    • 0344980313 scopus 로고    scopus 로고
    • The ternary complex of 10 did not afford satisfactory selectivity
    • The ternary complex of 10 did not afford satisfactory selectivity.
  • 33
    • 0344117741 scopus 로고    scopus 로고
    • Purification was carried out using silica gel column chromatography unless otherwise noted
    • Purification was carried out using silica gel column chromatography unless otherwise noted.


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