A novel separation technique of diastereomeric esters of pyridylethanols by extraction: Formal total synthesis of PNU-142721, HIV-1 reverse transcriptase inhibitor

Tetrahedron

Volumn 60, Issue 14, 2004, Pages 3311-3317

  Matsugi, Masato ^a   Itoh, Kinuyo ^a   Nojima, Masatomo ^a   Hagimoto, Yuri ^a   Kita, Yasuyuki ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

CH interaction; Chiral resolution; Diastereomers; Extraction; PNU 142721

Indexed keywords

1 FURO[2,3 C]PYRIDIN 5 YL ETHANOL; 6 CHLORO 2 [(1 FURO[2,3 C]PYRIDIN 5 YLETHYL)THIO] 4 PYRIMIDINAMINE; ALCOHOL DERIVATIVE; ETHER; HYDROCHLORIC ACID; PYRIDINE DERIVATIVE; RNA DIRECTED DNA POLYMERASE INHIBITOR; UNCLASSIFIED DRUG;

AQUEOUS SOLUTION; ARTICLE; CALCULATION; CHIRALITY; DIASTEREOISOMER; DRUG STRUCTURE; DRUG SYNTHESIS; EXTRACTION; HUMAN IMMUNODEFICIENCY VIRUS 1; MOLECULAR INTERACTION; PRIORITY JOURNAL; SEPARATION TECHNIQUE;

HUMAN IMMUNODEFICIENCY VIRUS 1;

EID: 1642265128     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2004.01.062     Document Type: Article

References (27)

1. Staunton J., Eisenbraun E. J. Org. Synth. 42:1962;4.
2. Djerassi C., Hart P.A., Warawa E.J. J. Am. Chem. Soc. 86:1964;78.
3. Matsugi M., Nojima M., Hagimoto Y., Kita Y. Tetrahedron Lett. 42:2001;8039.
4. Matsugi M., Itoh K., Nojima M., Hagimoto Y., Kita Y. Chem. Eur. J. 8:2002;5551.
5. For reviews of CH/π interactions, see: (a) Oki M. Acc. Chem. Res. 23:1990;351.
6. Etter M.C. J. Phys. Chem. 95:1991;4601.
7. Zaworotko M.J. Chem. Soc. Rev. 23:1994;283.
8. Nishio M., Umezawa Y., Hirota M., Takeuchi Y. Tetrahedron. 51:1995;8665.
9. Nishio M., Umezawa Y., Hirota M. The CH/π interaction. 1998;Wiley, New York.
10. Takagi T., Tanaka A., Matsuo S., Maezaki H., Tani M., Fujiwara H., Sasaki Y. J. Chem. Soc., Perkin Trans. 2. 1987;1015.
11. Suezawa H., Hashimoto T., Tsuchinaga K., Yoshida T., Yuzuri T., Sakakibara K., Hirota M., Nishio M. J. Chem. Soc., Perkin Trans. 2. 2000;1243.
12. Wishka D.G., Graber D.R., Seest E.P., Dolak L.A., Han F., Watt W., Morris J. J. Org. Chem. 63:1998;7851.
13. Lindberg J., Sigurosson S., Lowgren S., Andersson H.O., Sahlberg C., Noreen R., Fridborg K., Zhang H., Unge T. Eur. J. Biochem. 269:2002;1670.
14. Wishka D.G., Graber D.R., Kopta L.A., Olmsted R.A., Friis J.M., Hosley J.D., Adams W.J., Seest E.P., Castle T.M., Dolak L.A., Keiser B.J., Yagi Y., Jeganathan A., Schlachter S.T., Murphy M.J., Cleek G.J., Nugent R.A., Poppe S.M., Swaney S.M., Han F., Watt W., White W.L., Poel T.J., Thomas R.C., Voorman R.L., Stefanski K.J., Stehle R.G., Tarpley W.G., Morris J. J. Med. Chem. 41:1998;1357.
15. Uenishi J., Takagi T., Ueno T., Hiraoka T., Yonemitsu O., Tsukube H. Synlett. 1999;41.
16. For reviews of the enzyme-catalized acyl transfer, see: (a) Faber K., Riva S. Synthesis. 1992;895.
17. Carrea G., Riva S. Angew. Chem., Int. Ed. Engl. 39:2000;2226.
18. Okano K., Muraya K., Ikariya T. Tetrahedron Lett. 41:2000;9277.
19. These pyridylethanols were essentially prepared by according to the reported method: (a) Bellezza F., Cipiciani A., Cruciani G., Fringuelli F. J. Chem. Soc., Perkin Trans. 1. 2000;4439.
20. Trecourt F., Breton G., Bonnet V., Mongin F., Marsais F., Queguiner G. Tetrahedron. 56:2000;1349.
21. Bullitt O.H. Jr., Maynard J.T. J. Am. Chem. Soc. 76:1954;1370.
22. Uenishi J., Hiraoka T., Hata S., Nizhiwaki K., Yonemitsu O., Nakamura K. J. Org. Chem. 63:1998;2481.
23. D of the corresponding 1c after the removal of the steroid moiety: Seemayer R., Schneider M.P. Tetrahedron: Asymmetry. 3:1992;827.
24. Matsugi M., Itoh K., Nojima M., Hagimoto Y., Kita Y. Tetrahedron Lett. 42:2001;6903.
25. The structure of 3a and 4a was calculated using MOPAC program (PM3) in the CAChe system; Tektronix CAChe system, CAChe Scientific Inc, 1993.
26. Bondi A. J. Phys. Chem. 68:1964;441.
27. RS) of their esters with chiral non-racemic arylalcohols is reported; Ferreiro M.J., Latypov S.K., Quinñoá E., Riguera R. J. Org. Chem. 65:2000;2658.