A diastereoselective synthesis of (2S, 3R, 4S)2-amino-1-cyclohexyl-6-methylheptane-3,4-diol, the Abbott aminodiol

Tetrahedron Letters

Volumn 37, Issue 12, 1996, Pages 1961-1964

  Alexander, Christopher W ^a   Liotta, Dennis C ^a  

^a EMORY UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKANEDIOL DERIVATIVE;

ARTICLE; CHIRALITY; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STEREOCHEMISTRY; X RAY ANALYSIS;

EID: 0029876608     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00180-3     Document Type: Article

References (23)

1. (a) Luly, J. R.; Hsiao, C. -N.; BaMaung, N.; Plattner, J. J. J. Org. Chem. 1988, 53, 6109.
2. (b) Wood, J. L.; Jones, D. R.; Hirschmann, R.; Smith, III, A. B. Tetrahedron Lett. 1990, 31, 6329.
3. (c) Kobayashi, Y.; Matsumoto, T.; Takemoto, Y.; Nakatani, K.; Ito, Y.; Kamijo, T.; Harada, H.; Terashima, S. Chem. Pharm. Bull. 1991, 39, 2550.
4. (d) Chan, M. F.; Hsiao, C. Tetrahedron Lett. 1992, 33, 3567.
5. (e) Baker, W. R.; Condon, S. L. J. Org. Chem. 1993, 58, 3277.
6. (f) Krysan, D. J.; Haight, A. R.; Menzia, J. A.; Welch, N. Tetrahedron 1994, 50, 6163.
7. (g) Spero, D. M.; Kapadia, S.; Farina, V. Tetrahedron Lett. 1995, 36, 4543.
8. Kleinert, H. D.; Rosenburg, S. H.; Baker, W. R.; Stein, H. H.; Klinghofer, V.; Barlow, J.; Spina, K.; Polakowski, J.; Kovar, P.; Cohen, J.; Denissen, J. Science 1992, 257, 1940 and references cited therein.
9. Reetz, M. T. Angew. Chem. Int. Ed. Engl. 1991, 30, 1531.
10. (a) Goh, J. B.; Lagu, B. R.; Wurster, J; Liotta, D. C. Tetrahedron Lett. 1994, 35, 6029.
11. (b) Lagu, B. R.; Liotta, D. C. Tetrahedron Lett. 1994, 35, 4485.
12. (c) Lagu, B. R.; Crane, H. M.; Liotta, D. C. J. Org. Chem. 1993, 58, 4191.
13. Schuda, P. F.; Greenlee, W. J.; Chakravarty, P. K.; Eskola, P. J. Org. Chem. 1988, 53, 873.
14. (a) Reetz, M. T.; Drewes, M. W.; Schmitz. A. Angew. Chem. Int. Ed. Engl. 1987, 26, 1141.
15. (b) Cooke, J. W. B.; Davies, S. G.; Naylor, A. Tetrahedron 1993, 49, 7955.
16. Reetz, M. T.; Drewes, M. W.; Lennick, K.; Schmitz, A.; Holdgrün, X. Tetrahedron: Asymmetry 1990, 1, 375.
17. (a) Davis, F. A.; Stringer, O. D. J. Org. Chem. 1982, 47, 1774.
18. (b) Bunnage, M. E.; Chernega, A. N.; Davies, S. G.; Goodwin, C. J. J. Chem. Soc. Perkin Trans. 1, 1994, 2373.
19. Ram, S.; Spicer, L. D. Tetrahedron Lett. 1987, 28, 515.
20. 13C NMR, IR, MS, and C, H, N analysis.
21. Lohray, B. B. Synthesis 1992, 1035.
22. Luly, J. R.; BaMuang, N.; Soderquist, J.; Fung, A. K. L.; Stein, H.; Kleinert, H. D.; Marcotte, P. A.; Egan, D. A.; Bopp, B.; Merits, I.; Bolis, G.; Greer, J.; Perun, T. J.; Plattner, J. J. J. Med. Chem. 1988, 31, 2264.
23. The enantiopurity of the 9 was assayed by chiral HPLC analysis using a Shimadzu system, (LC-6A pumps, SPD-6A UV detector, and C-R6A integrator), equipped with a Daicel Chiralcel OD column (UV detector: 240 nm; solvent system: 99% hexanes: 1% 2-propanol; flow rate: 0.8 mL/min.; ambient temperature). Retention times: N-Boc diol 9: 25.295 min (broad peak), and ± 9: 25.133 min and 27.662 min (broad peaks).