Enantioselective synthesis of pantolactone analogues from an ephedrine-derived morpholine-dione

Tetrahedron

Volumn 59, Issue 18, 2003, Pages 3275-3282

  Pansare, Sunil V ^a   Bhattacharyya, Annyt ^a  

^a NATIONAL CHEMICAL LABORATORY   (India)

Author keywords

Asymmetric synthesis; Dehydration; Lactones; Prins reaction; Reduction

Indexed keywords

2 (1 METHOXYMETHYL)CYCLOHEXYL 4,5 DIMETHYL 6 PHENYLMORPHOLIN 3 ONE; 2 CYCLOHEXYL 2 HYDROXY 4,5 DIMETHYL 6 PHENYLMORPHOLIN 3 ONE; 2 CYCLOHEXYLIDENE 4,5 DIMETHYL 6 PHENYLMORPHOLIN 3 ONE; 2 HYDROXY 2 (1 METHOXYMETHYL)CYCLOHEXYL N METHYLACETAMIDE; 2 HYDROXY 3 (METHOXYMETHYL) N 3 DIMETHYLPENTANAMIDE; 2 SEC BUTYL 2 HYDROXY 4,5 DIMETHYL 6 PHENYLMORPHOLIN 3 ONE; 2 [1 (METHOXYMETHYL) 1 METHYLPROPYL] 4,5 DIMETHYL 6 PHENYLMORPHOLIN 3 ONE; 3,4 DIMETHYL 2 PHENYL 1,14,16 TRIOXA 4 AZADISPIRO[5.0.5.4]HEXADECAN 5 ONE; 4 ETHYL 3 HYDROXY 4 METHYLDIHYDROFURAN 2 ONE; 4 HYDROXY 2 OXASPIRO[4,5]DECAN 3 ONE; 4,5 DIMETHYL 2 (1 METHYLPROPYLIDENE) 6 PHENYLMORPHOLIN 3 ONE; 4,5 DIMETHYL 6 PHENYLMORPHOLIN 2,3 DIONE; 5 ETHYL 5,9,10 TRIMETHYL 8 PHENYL 1,3,7 TRIOXA 10 AZASPIRO[5.5]UNDECAN 11 ONE; ALKENE DERIVATIVE; AMIDE; FURAN DERIVATIVE; GAMMA BUTYROLACTONE DERIVATIVE; MORPHOLINE DERIVATIVE; PANTOLACTONE; SPIRO COMPOUND; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHIRALITY; ENANTIOSELECTIVITY; PRIORITY JOURNAL; SYNTHESIS;

EID: 0037471491     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(03)00408-3     Document Type: Article

References (27)

1. (a) Peterson, M.; Kalbermatten, G. PCT Int. Appl. WO 2001018231 A2, 2001.
2. (b) Nakano T., Oh-Hashi N., Ino Y., Nagai Y. Main Group Met. Chem. 23:2000;259.
3. (c) Eliel E.L., Bai X., Ohwa M. J. Chin. Chem. Soc. 47:2000;63.
4. (d) Blandin V., Carpentier J.-F., Mortreaux A. Eur. J. Org. Chem. 1999;1787.
5. (e) Pansare S.V., Shinkre B.A., Bhattacharyya A. Tetrahedron. 58:2002;8985.
6. (a) Ballini R., Marcantoni E., Petrini M. J. Chem. Soc., Perkin Trans. 1. 1991;490.
7. (b) Kabeya M., Hamada Y., Shioiri T. Tetrahedron. 53:1997;9769.
8. (c) Okabe M., Sun R.-C., Zenchoff G.B. J. Org. Chem. 56:1991;4392.
9. (a) Sefkow M. J. Org. Chem. 66:2001;2343.
10. (b) Ueki T., Ichinari D., Yoshihara K., Morimoto Y., Kinoshita T. Tetrahedron Lett. 39:1998;667.
11. (c) Ichinari D., Ueki T., Yoshihara K., Kinoshita T. Chem. Commun. 1997;1743.
12. Lacrampe, J. F.; Armand, F.; Eddy, E. J.; Deroose, D. F.; Fortin, J. M. C.; Coesemans, E. PCT Int. Appl. WO 0110866 A1 20010215, 2001.
13. For studies on the resolution and enantioselective synthesis of pantolactone, see (a) Kesseler, M.; Hauer, B.; Friedrich, T.; Mattes, R. PCT Int. Appl. WO 2001032890 A1, 2001. (b) Pansare S.V., Jain R.P. Org. Lett. 2:2000;175 (c) Haughton L., Williams J.M., Zimmerman J.A. Tetrahedron: Asymmetry. 11:2000;1697 (d) Paetow M., Ahrens D., Hoppe D. Tetrahedron Lett. 33:1992;5323. and references cited therein.
14. For studies on the resolution and enantioselective synthesis of pantolactone, see (a) Kesseler, M.; Hauer, B.; Friedrich, T.; Mattes, R. PCT Int. Appl. WO 2001032890 A1, 2001. (b) Pansare S.V., Jain R.P. Org. Lett. 2:2000;175 (c) Haughton L., Williams J.M., Zimmerman J.A. Tetrahedron: Asymmetry. 11:2000;1697 (d) Paetow M., Ahrens D., Hoppe D. Tetrahedron Lett. 33:1992;5323. and references cited therein.
15. For studies on the resolution and enantioselective synthesis of pantolactone, see (a) Kesseler, M.; Hauer, B.; Friedrich, T.; Mattes, R. PCT Int. Appl. WO 2001032890 A1, 2001. (b) Pansare S.V., Jain R.P. Org. Lett. 2:2000;175 (c) Haughton L., Williams J.M., Zimmerman J.A. Tetrahedron: Asymmetry. 11:2000;1697 (d) Paetow M., Ahrens D., Hoppe D. Tetrahedron Lett. 33:1992;5323. and references cited therein.
16. For studies on the resolution and enantioselective synthesis of pantolactone, see (a) Kesseler, M.; Hauer, B.; Friedrich, T.; Mattes, R. PCT Int. Appl. WO 2001032890 A1, 2001. (b) Pansare S.V., Jain R.P. Org. Lett. 2:2000;175 (c) Haughton L., Williams J.M., Zimmerman J.A. Tetrahedron: Asymmetry. 11:2000;1697 (d) Paetow M., Ahrens D., Hoppe D. Tetrahedron Lett. 33:1992;5323. and references cited therein.
17. (a) Fissekis J.D., Skinner C.G., Shive W. J. Am. Chem. Soc. 82:1960;1654 (b) Klar, U.; Schwede, W.; Skuballa, W.; Buchmann, B.; Schriner, M. Ger. Offen. DE 19735574 A1 19990211, 1999 (CAN 130: 168162).
18. (a) Fissekis J.D., Skinner C.G., Shive W. J. Am. Chem. Soc. 82:1960;1654 (b) Klar, U.; Schwede, W.; Skuballa, W.; Buchmann, B.; Schriner, M. Ger. Offen. DE 19735574 A1 19990211, 1999 (CAN 130: 168162).
19. Imada Y., Mitsue Y., Ike K., Washizuka K.-I., Murahashi S.-I. Bull. Chem. Soc. Jpn. 69:1996;2079.
20. The stereochemical assignment is based on the reported trend in chemical shifts for the olefinic methine protons in E and Z benzylidene camphor derivatives: Kossanyi J., Furth B., Morizur J.P. Tetrahedron. 26:1970;395.
21. For reviews on the Prins reaction, see: (a) Adams D.R., Bhatnagar S.P. Synthesis. 1977;661 (b) Snider B.B. Compr. Org. Synth. 2:1991;527.
22. For reviews on the Prins reaction, see: (a) Adams D.R., Bhatnagar S.P. Synthesis. 1977;661 (b) Snider B.B. Compr. Org. Synth. 2:1991;527.
23. Pansare S.V., Ravi R.G., Jain R.P. J. Org. Chem. 63:1998;4120.
24. Deslongchamps P. Stereoelectronic Effects in Organic Chemistry. 1989;Pergamon, New York. Chapter 2.
25. Tadano K., Kanazawa S., Ogawa S. J. Org. Chem. 53:1988;3868.
26. Ueki T., Ichinari D., Yoshihara K., Morimoto Y., Kinoshita T. Tetrahedron Lett. 39:1998;667.
27. Herz W., Bruno M. Phytochemistry. 26:1987;1175.