Stereoselective synthesis of (4S,5R,6S)-4-(5,6-epoxy-6-phenyl)-γ-lactone

Tetrahedron Asymmetry

Volumn 7, Issue 6, 1996, Pages 1797-1810

  Solladié Cavallo, Arlette ^a   Roche, Didier ^a   Bold, Guido ^b   Acemoglu, Figan ^b   Tintelnot Blomley, Marina ^b   Fischer, Jean ^c   De Cian, André ^c  

^a EHICS   (France)

^b CIBA GEIGY LTD   (Switzerland)

^c CNRS   (France)

Author keywords

[No Author keywords available]

Indexed keywords

4 (5,6 EPOXY 6 PHENYL) GAMMA LACTONE; LACTONE DERIVATIVE; PROPIONAMIDE DERIVATIVE; PROTEINASE INHIBITOR; UNCLASSIFIED DRUG; VALINE;

ARTICLE; DRUG SYNTHESIS; ENANTIOMER; HUMAN IMMUNODEFICIENCY VIRUS 1; MOLECULAR MODEL; PRIORITY JOURNAL; STEREOCHEMISTRY;

EID: 0343026674     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/0957-4166(96)00215-7     Document Type: Article

References (18)

1. H.G., Capraro ; G., Bold ; A., Fässler ; R. Cozens ; J., Mestan ; B., Poncioni ; J.L., Rösel ; D., Stover ; M., Lang Arch. Pharm. (Pharmac. Med. Chem.) , in press.
2. a) A., Wlodawer Pharmacotherapy 1994, 14, 98.
3. b) J.A., Martin ; S., Redshaw ; G.J., Thomas Prog. Med. Chem. 1995, 32, 239.
4. c) M.L., West ; D.P., Fairlie TiPS 1995, 16, 67.
5. M., Miller ; J., Schneider ; B.K., Sathyanarayana ; M.V. Toth ; G.R., Marshall ; L. Clawson ; L., Selk ; St.B.H., Kent ; A., Wlodawer Science, 1989, 246, 1149.
6. L.V., Yerino ; M.E., Osborn ; P.S., Mariano Tetrahedron Lett. 1982, 38, 1579.
7. M.M., Midland ; A., Tramontano ; A., Kazubski ; R.S., Graham ; D.J.S., Tsai ; D., Cardin Tetrahedron 1984, 40, 1371. (S)-Alpine-borane, prepared from (-)-α-pinene, provides (S)-propargyl alcohols.
8. Commercialy available (S)-Alpine-borane is 82% ee only.
9. H.C., Brown ; G.G., Pai J. Org. Chem. 1985, 50, 1384, running the reaction without solvent improves the optical purity of the alcohols.
10. a) G., Berti Topics in Stereochemistry 1973, vol. 7, 130, Ed. John Wiley & sons, Inc.
11. b) P., Chautemps ; J.L., Pierre Tetrahedron 1976, 32, 549.
12. A., Lüttringhams ; R., Schneider Ann. Chem. 1964, 679, 123.
13. R., Hanko ; K., Rabe ; R., Daily ; D., Hoppe Angew. Chem. 1991, 103, 1725.
14. Compounds 11a, 11b, 12a and 12b and the corresponding sulfoxides have been tested by Dr. J. Rösel in the HIV-1 protease inhibition assay (E., Altery ; G., Bold ; R., Cozens ; A., Fässler ; Th., Klimkait ; M., Lang ; J., Lazdins ; B., Poncioni ; J.L., Rösel ; P., Schneider ; M., Walker ; K., Woods-Cook Antimicr. Agents Chemther. 1993, 37, 2087). These compounds exerted only a weak inhibitory effect : those with the lowest IC50 values were 12a (42 μM) and the corresponding sulfoxide (40 μM) as well as the sulfoxide corresponding to 11a (28 μM).
15. J.P., Vigneron ; R., Méric ; M., Larchevêque ; A., Debal ; J.Y., Lallemand ; G., Kunesch ; P., Zagatti ; M., Gallois Tetrahedron, 1984, 40, 3521.
16. Calculations using Classical Mechanics (MM2) were done on a CAChe WorkSystem from CAChe Scientific, Oxford Molecular.
17. While this paper was to be sent, the SADDLE calculations of .M. Rogic appeared : J. Org. Chem. 1996, 61, 1341.
18. It is worth noting that Narula's model (A.S., Narula Tetrahedron Lett. 1983, 24, 5421) would have predicted the observed (5R,6S) configuration for the hydroxy-epoxide 6.