Stereocontrolled synthesis of pseudo C2-symmetric 1,3-diamino-2-propanol core units of HIV protease inhibitors

Tetrahedron Letters

Volumn 38, Issue 3, 1997, Pages 499-502

  Dondoni, Alessandro ^a   Perrone, Daniela ^a  

^a UNIVERSITY OF FERRARA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

PROPANOLAMINE DERIVATIVE; PROTEINASE INHIBITOR;

ARTICLE; CHIRALITY; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION ANALYSIS; STEREOISOMERISM;

EID: 0031012362     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(96)02355-6     Document Type: Article

References (19)

1. (a) Erickson, J.; Neidhart, D. J.; VanDrie, J.; Kempf, D. J.; Wang, X. C.; Norbeck, D. W.; Plattner, J. J.; Rittenhouse, J. W.; Turon, M.; Wideburg, N.; Kohlbrenner, W. E.; Simmer, R.; Helfrich, R.; Paul, D. A.; Knigge, M. Science 1990, 249, 527.
2. (b) Kempf, D. J.; Norbeck, D. W.; Codacovi, L. M.; Wang, X. C.; Kohlbrenner, W. E.; Wideburg, N. E.; Paul, D. A.; Knigge, M. F.; Vasavanonda, S.; Craig-Kennard, A.; Saldivar, A.; Rosenbrook Jr., W.; Clement, J. J.; Plattner, J. J.; Erickson, J. J. Med. Chem. 1990, 33, 2687.
3. (a) Kempf, D. J.; Sowin, T. J. Doherty, E. M.; Hannick, S. M.; Codavoci, L. M.; Henry, R. F.; Green, B. E.; Spanton, S. G.; Norbeck, D. W. J. Org. Chem. 1992, 57, 5692.
4. (b) Wittenberger, S. J.; Baker, W. R.; Donner, B. G. Tetrahedron 1993, 49, 1547.
5. By virtue of its symmetrical characteristics, the central carbon becomes nonstereogenic in the final product.
6. Enders, D.; Jegelka, U.; Dücker, B. Angew. Chem. Int. Ed. Engl. 1993, 32, 423.
7. a) Dondoni, A.; Perrone, D. Synthesis 1993, 1162.
8. b) Dondoni, A.; Perrone, D. J. Org. Chem. 1995, 60, 4749.
9. c) Dondoni, A.; Perrone, D.; Semola, M. T. J. Org. Chem. 1995, 60, 7927.
10. d) Dondoni, A.; Perrone, D.; Merino, P. J. Org. Chem. 1995, 60, 8074.
11. Dondoni, A.; Franco, S.; Junquera, F.; Merchan, F. L.; Merino, P.; Tejero, T.; Bertolasi, V. Chem. Eur. J. 1995, 1, 505.
12. Dondoni, A.; Junquera, F.; Merchan, F. L.; Merino, P.; Tejero, T. Synthesis 1993, 1450.
13. Dondoni, A.; Junquera, F.; Merchan, F. L.; Merino, P.; Tejero, T. Tetrahedron Lett. 1994, 35, 9439.
14. 1H NMR analysis.
15. 13C NMR spectra (300 MHz).
16. 3) δ: 2.50 (dd, 1 H, J = 10.1, 13.4 Hz), 2.65 (dd, 1 H, J = 9.6, 13.4 Hz), 2.91 (dd, 1 H, J = 4.6, 13.4 Hz), 3.01 (dd, 1 H, J = 3.2, 13.4 Hz), 3.08-3.20 (m, 1 H), 3.31-3.43 (m, 2 H), 7.15-7.45 (m, 10 H).
17. 1H NMR.
18. Compounds 8 and 9 (the latter is not shown in Scheme 3) were not separated.
19. 3) δ: 2.52 (dd, 2 H, J = 10.1, 13.5 Hz), 3.17 (dd, 2 H, J = 3.0, 13.5 Hz), 3.29 (ddd, 2 H, J = 3.0, 5.7, 10.1 Hz), 3.39 (t, 1 H, J = 5.7 Hz), 7.17-7.40 (m, 10 H).