Remarkable stereocontrol in the synthesis of 1,2,3,5-tetrasubstituted tetrahydropyrans via an asymmetric heterocycloaddition of a ketone-derived enol ether

Tetrahedron Letters

Volumn 44, Issue 10, 2003, Pages 2141-2144

  Gong, Junfang ^a   Bonfand, Eric ^b   Brown, Eric ^b   Dujardin, Gilles ^b   Michelet, Véronique ^a   Genêt, Jean Pierre ^a  

^a PSL RESEARCH UNIVERSITY   (France)

^b UNIVERSITÉ DU MAINE   (France)

Author keywords

Acetal reduction; Asymmetric hetero Diels Alder; Chiral C glycosides; Ketone derived enol ether; Stereocontrolled hydrogenation

Indexed keywords

ACETAL; CHARCOAL; ETHER DERIVATIVE; ETHYLAMINE; ETHYLDIISOPROPYLAMINE; KETONE DERIVATIVE; MANDELIC ACID; PALLADIUM; TETRAHYDROPYRAN DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHIRALITY; CYCLOADDITION; DIELS ALDER REACTION; HYDROGENATION; ISOMER; REDUCTION; STEREOCHEMISTRY; SYNTHESIS;

BETULACEAE;

EID: 0037416845     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(03)00162-X     Document Type: Article

References (59)

1. Suhadolnik R.J. Nucleoside Antibiotics. 1970;Wiley-Interscience, New York.
2. Du Y., Linhardt R.J., Vlahov I.R. Tetrahedron. 54:1998;9913-9959.
3. Nicotra F. Topics Curr. Chem. 187:1997;55-83.
4. Sinaÿ P. Pure Appl. Chem. 69:1997;459-463.
5. Beau J.-M., Gollagher T. Topics Curr. Chem. 187:1997;1-54.
6. Postema M.H.D. C-Glycoside Synthesis. 1995;CRC Press, Boca Raton.
7. Levy D.E., Tang C. The Chemistry of C-Glycosides. 1995;Pergamon, Oxford.
8. Michelet V., Adiey K., Bulic B., Genêt J.-P., Dujardin G., Rossignol S., Brown E., Toupet L. Eur. J. Org. Chem. 1999;2885-2892. and references cited therein.
9. Ringel S.M., Greenough R.C., Roemer S., Connor D., Gutt A.L., Blair B., Kanter G., von Strandtmann M. J. Antibiot. 30:1977;371-375 Levine, H. B.; Ringel, S. M. Proceeding of the Third International Coccidioidomycosis Symposium, June 1977, pp. 318-322.
10. Ringel S.M., Greenough R.C., Roemer S., Connor D., Gutt A.L., Blair B., Kanter G., von Strandtmann M. J. Antibiot. 30:1977;371-375 Levine, H. B.; Ringel, S. M. Proceeding of the Third International Coccidioidomycosis Symposium, June 1977, pp. 318-322.
11. Knauth P., Reichenbach H. J. Antibiot. 53:2000;1182-1190.
12. Kende A.S., Fujii Y., Mendoza J.S. J. Am. Chem. Soc. 112:1990;9645-9646.
13. Kende A.S., Mendoza J.S., Fujii Y. Tetrahedron. 49:1993;8015-8038.
14. Mendoza J.S., Kende A.S. Recent Prog. Chem. Synth. Antibiot. Relat. Microb. Prod. 1993;405-433.
15. Kirkland T.A., Colucci J., Geraci L.S., Marx M.A., Schneider M., Kaelin D.E. Jr., Martin S.F. J. Am. Chem. Soc. 123:2001;12432-12433.
16. Lee E., Choi S.J., Kim H., Han H.O., Kim Y.K., Min S.J., Son S.H., Lim S.M., Jang W.S. Angew. Chem., Int. Ed. 41:2002;176-178.
17. Liu P., Jacobsen E.N. J. Am. Chem. Soc. 123:2001;10772-10773.
18. Horton P.A., Koehn F.E., Longley R.E., McConnell O.J. J. Am. Chem. Soc. 116:1994;6015-6016.
19. Lee E., Song H.Y., Kang J.W., Kim D.-S., Jung C.-K., Joo J.M. J. Am. Chem. Soc. 124:2002;384-385.
20. Yotsu-Yamashita M., Haddock R.L., Yasumoto T. J. Am. Chem. Soc. 115:1993;1147-1148.
21. Fujiwara K., Murai A., Yotsu-Yamashita M., Yasumoto T. J. Am. Chem. Soc. 120:1998;10770-10771.
22. Paquette L.A., Barriault L., Pissarnitski D., Johnston J.N. J. Am. Chem. Soc. 122:2000;619-631.
23. White J.D., Blackmore P.R., Browder C.C., Hong J., Lincoln C.M., Nagornyy P.A., Robarge L.A., Wardrop D.J. J. Am. Chem. Soc. 123:2001;8593-8595.
24. Christmann M., Bhatt U., Quitschalle M., Claus E., Kalesse M. Angew. Chem., Int. Ed. 39:2000;4364-4366.
25. Bhatt U., Christmann M., Quitschalle M., Claus E., Kalesse M. J. Org. Chem. 66:2001;1885-1893.
26. Williams D.R., Ihle D.C., Plummer S.V. Org. Lett. 3:2001;1383-1386.
27. Ingenhorst G., Bindseil K.U., Boddien C., Dröse S., Gassel M., Altendorf K., Zeeck A. Eur. J. Org. Chem. 2001;4525-4532.
28. Boger D.L., Weinreb S.N. Hetero Diels-Alder Methodology in Organic Synthesis. 1987;Academic Press, San Diego.
29. Waldmann H. Synthesis. 1994;535-555.
30. Tietze L.F., Kettschau G. Top. Curr. Chem. 189:1997;1-120.
31. Rück-Braun K., Kunz H. Chiral Auxiliaries in Cycloadditions. 1999;Wiley-VCH, Weinheim.
32. Carmona D., Lamata P.M., . Oro L.A. Coord. Chem. Rev. 2000;717-772.
33. Jorgensen K.A. Angew. Chem., Int. Ed. 39:2000;3558-3588.
34. Thorhauge J., Johannsen M., Jorgensen K.A. Angew. Chem., Int. Ed. 37:1998;2404-2406.
35. Evans D.A., Olhava E.J., Johnson J.S., Janey J.M. Angew. Chem., Int. Ed. 37:1998;3372-3375.
36. Zhuang W., Thorhauge J., Jorgensen K.A. Chem. Commun. 2000;459-460.
37. Audrain H., Thorhauge J., Hazell R.G., Jorgensen K.A. J. Org. Chem. 65:2000;4487-4497.
38. Evans D.A., Johnson J.S., Olhava E.J. J. Am. Chem. Soc. 122:2000;1635-1649.
39. Gademann K.G., Chavez D.E., Jacobsen E.N. Angew.Chem., Int. Ed. 41:2002;3059-3061.
40. Dujardin G., Rossignol S., Brown E. Tetrahedron Lett. 37:1996;4007-4010.
41. Dujardin G., Rossignol S., Brown E. Synthesis. 1998;763-770.
42. Dujardin G., Rossignol S., Brown E. Tetrahedron Lett. 36:1995;1653-1656.
43. Takai K., Kakiuchi T., Kataoka Y. J. Org. Chem. 59:1994;2668-2670.
44. Postema M.H.D., Calimente D., Liu L., Behrmann T.L. J. Org. Chem. 65:2000;6061-6068.
45. 1H NMR (400 MHz) on the crude material.
46. Martel A., Leconte S., Dujardin G., Brown E., Maisonneuve V., Retoux R. Eur. J. Org. Chem. 2002;514-525.
47. Boger D.L., Robarge K.D. J. Org. Chem. 53:1988;5793-5796.
48. Werschkun B., Thiem J. Synthesis. 1999;121-137.
49. Bennasar M.-L., Zulaica E., Juan C., Llauger L., Bosch J. Tetrahedron Lett. 40:1999;3961-3964.
50. Tietze L.F., Hartfiel U. Tetrahedron Lett. 31:1990;1697-1700.
51. Bach P., Lohse A., Bols M. Tetrahedron Lett. 40:1999;367-370.
52. 3) δ 5.46 (6), 5.26 (epi-6), 5.14 (7) ppm. The relative stereochemistry of alcohol 7 was not established.
53. A lack of selectivity was recently observed in the catalytic hydrogenation of bicyclic 1,1′,2,3,5-substituted dihydro-pyrans: Martel, A.; Dujardin, G.; Brown, E. Synthesis 2003, in press.
54. 7: C, 67.22 H, 8.68, Found: C, 67.45 H, 8.73.
55. Lewis M.D., Cha J.K., Kishi Y. J. Am. Chem. Soc. 104:1982;4976-4977.
56. Lasterra Sanchez M.E., Michelet V., Besnier I., Genêt J.-P. Synlett. 1994;705-708.
57. Michelet V., Dujardin G., Genêt J.-P. Tetrahedron Lett. 38:1997;7741-7744.
58. Bartels B., Hunter R. J. Org. Chem. 58:1993;6756-6765.
59. 4: 259.1909, found: 259.1915.