A simple stereoselective synthesis of the cholesterol absorption inhibitor (-)-SCH 48461

Synthesis

Volumn , Issue 7, 1996, Pages 819-820

  Braun, Manfred ^a   Galle, Dietmar ^a  

^a HEINRICH HEINE UNIVERSITY   (Germany)

Author keywords

1,1,2 triphenylethane 1,2 diol; circular dichroism; esterenelate imine condensation; lactam

Indexed keywords

1,4 BIS(4 METHOXYPHENYL) 3 (3 PHENYLPROPYL) 2 AZETIDINONE; ANTILIPEMIC AGENT;

ARTICLE; DRUG STRUCTURE; DRUG SYNTHESIS; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0029929183     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1996-4302     Document Type: Article

References (18)

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2. Morin, R. B.; Gorman, M. Chemistry and Biology of β-Lactam-Antibiotics; Vol. 1-3; Academic: New York, 1982. Georg, G. I., Ed. The Organic Chemistry of β-Lactams; VCH: Weinheim, 1993. Hart, D. J.; Ha, D.-C. Chem. Rev. 1989, 59, 1447.
3. Morin, R. B.; Gorman, M. Chemistry and Biology of β-Lactam-Antibiotics; Vol. 1-3; Academic: New York, 1982. Georg, G. I., Ed. The Organic Chemistry of β-Lactams; VCH: Weinheim, 1993. Hart, D. J.; Ha, D.-C. Chem. Rev. 1989, 59, 1447.
4. Burnett, D. A.; Caplen, M. A.; Davis, H. R., Jr.; Burrier, R. E.; Clader, J. W. J. Med. Chem. 1994, 37, 1733.
5. Burnett, D. A. Tetrahedron Lett. 1944, 35, 7339.
6. Braun, M.; Sacha, H.; Galle, D.; El-Alali, A. Tetrahedron Lett. 1995, 36, 4213.
7. Braun, M.; Gräf, S.; Herzog, S. Org. Synth. 1993, 72, 32.
8. Fieser, L. F.; Berliner, E.; Bondhus, F. J.; Chang, F. C.; Dauben, W.G.; Ettlinger, M.G.; Fawaz, G.; Fields, M.; Heidelberger, C.; Heymann, H.; Vaughan, W. R.; Wilson, A. G.; Wilson, E.; Wu, M.-i.; Leffler, M. T.; Hamlin, K. E.; Matson, E. J.; Moore, E. E.; Moore, M. B.; Zaugg, H. E. J. Am. Chem. Soc. 1948, 70, 3174.
9. Hantzsch, A.; Schwab, O. Ber. Dtsch. Chem. Ges. 1901, 34, 822.
10. In the cis-isomer of 1, the doublet (J = 6 Hz) of 4-H is observed at δ = 5.11 (see Ref. 2) which differs distinctly from the corresponding signal of 1 synthesized by us (see experimental).
11. 3 = Tris[3-(2,2,3,3,4,4,4-heptafluoro-1-hydroxybutylidene)-d-camphorato]europium (Aldrich)
12. Braun, M.; Devant, R. Tetrahedron Lett. 1984, 25, 5031. Braun, M. Angew. Chem. 1987, 99, 24; Angew. Chem. Int. Ed. Engl. 1987, 26, 24. Braun, M.; Sacha, H. J. Prakt. Chem. 1993, 335, 653.
13. Braun, M.; Devant, R. Tetrahedron Lett. 1984, 25, 5031. Braun, M. Angew. Chem. 1987, 99, 24; Angew. Chem. Int. Ed. Engl. 1987, 26, 24. Braun, M.; Sacha, H. J. Prakt. Chem. 1993, 335, 653.
14. Braun, M.; Devant, R. Tetrahedron Lett. 1984, 25, 5031. Braun, M. Angew. Chem. 1987, 99, 24; Angew. Chem. Int. Ed. Engl. 1987, 26, 24. Braun, M.; Sacha, H. J. Prakt. Chem. 1993, 335, 653.
15. Braun, M.; Devant, R. Tetrahedron Lett. 1984, 25, 5031. Braun, M. Angew. Chem. 1987, 99, 24; Angew. Chem. Int. Ed. Engl. 1987, 26, 24. Braun, M.; Sacha, H. J. Prakt. Chem. 1993, 335, 653.
16. Galle, D.; Tolksdorf, M.; Braun, M. Tetrahedron Lett. 1995, 36, 4217, and references given therein.
17. MOPAC 6.0 package: Stewart, J. J. P. QCPE #455.
18. Devant, R.; Mahler, U.; Braun, M. Chem. Ber. 1988, 121, 397.