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Volumn 38, Issue 22, 1999, Pages 3373-3375

Stereoselective Mukaiyama-Michael/Michael/aldol domino cyclization as the key step in the synthesis of pentasubstituted arenes: An efficient access to highly active inhibitors of cholesteryl ester transfer protein (CETP)

Author keywords

Asymmetric synthesis; Cyclizations; Domino reactions; Drug research; Mukaiyama Michael additions

Indexed keywords

CARRIER PROTEIN; CHOLESTEROL ESTER; POLYCYCLIC AROMATIC HYDROCARBON; PROTEIN INHIBITOR;

EID: 0033571360     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3773(19991115)38:22<3373::AID-ANIE3373>3.0.CO;2-F     Document Type: Article
Times cited : (54)

References (30)
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    • note
    • 1 p.o. (p.o. = per os, oral administration).
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    • g) L. F. Tietze, U. Beifuss, Angew. Chem. 1993, 105, 137-170; Angew. Chem. Int. Ed. Engl. 1993, 32, 131-163;
    • (1993) Angew. Chem. Int. Ed. Engl. , vol.32 , pp. 131-163
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    • h) M. Ihara, K. Fukumoto, Angew. Chem. 1993, 105, 1054-1071; Angew. Chem. Int. Ed. Engl. 1993, 32, 1010-1022;
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    • Ihara, M.1    Fukumoto, K.2
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    • h) M. Ihara, K. Fukumoto, Angew. Chem. 1993, 105, 1054-1071; Angew. Chem. Int. Ed. Engl. 1993, 32, 1010-1022;
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  • 26
    • 0344801802 scopus 로고    scopus 로고
    • note
    • 4 in a ratio of 3:1 or by parallel addition of both components. A modification of this reaction has meanwhile been carried out on a kilogram scale.
  • 27
    • 0344369938 scopus 로고    scopus 로고
    • note
    • 1H NMR spectra suggest a hydrogen bond between the two groups (low-field shift and W-coupling of the OH hydrogen atom with an H atom of the neighboring AB system). By complexation with titanium this conformation should be maintained in the reaction mixture. Thus, the π orbitals of the carhonyl group and the σ C-H bond in the α position are almost orthogonal to each other. Therefore, acidification of the α H atom lacks conjugative stabilisation. In addition, elimination leads to greater steric hindrance of the neighboring substituents.
  • 28
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    • note
    • 1H NMR spectrum of this diastereomer indicates the absence of the intramolecular hydrogen bridge.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.