Carbohydrate-based oxepines: Ring expanded glycals for the synthesis of septanose saccharides

Tetrahedron Letters

Volumn 44, Issue 21, 2003, Pages 4057-4061

  Peczuh, Mark W ^a   Snyder, Nicole L ^a  

^a UNIVERSITY OF CONNECTICUT   (United States)

Author keywords

Glycal; Oxepine; Ring closing metathesis; Septanose carbohydrate

Indexed keywords

ALKADIENE; CARBOHYDRATE DERIVATIVE; ETHER DERIVATIVE; HEPTOSE; OXEPINE DERIVATIVE;

ARTICLE; CARBOHYDRATE ANALYSIS; CARBOHYDRATE SYNTHESIS; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYST; CYCLIZATION; OXYGENATION; PROTON NUCLEAR MAGNETIC RESONANCE; RING CLOSING METATHESIS; STEREOCHEMISTRY;

EID: 0038327845     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(03)00849-9     Document Type: Article

References (50)

1. Tran T.Q., Stevens J.D. Aust. J. Chem. 55:2002;171-178. and references cited therein.
2. Paluski Z. Polish J. Chem. 70:1996;667-707.
3. Eschenmoser A. Science. 284:1999;2118-2124.
4. Gellman S.H. Acc. Chem. Res. 31:1998;173-180.
5. Gademan K., Ernst M., Hoyer D., Seebach D. Angew. Chem., Int. Ed. 38:1999;1223-1226.
6. Porter E.A., Wang X., Lee H.-S., Weisblum B., Gellman S.H. Nature. 404:2000;585.
7. Gordon M.T., Lowary T.L., Hadad C.M. J. Am. Chem. Soc. 121:1999;9682-9692.
8. Ernst S., Venkataraman G., Sasisekharan V., Langer R., Cooney C.L., Sasisekharan R. J. Am. Chem. Soc. 120:1998;2099-2107.
9. Danishefsky S.J., Bilodeau M.T. Angew. Chem., Int. Ed. Engl. 35:1996;1380-1419.
10. Seeberger P.H., Eckhardt M., Gutteridge C.E., Danishefsky S.J. J. Am. Chem. Soc. 119:1997;10064-10072.
11. Plante O., Seeberger P.H. J. Org. Chem. 63:1998;9150-9151.
12. Halcomb R.L., Danishefsky S.J. J. Am. Chem. Soc. 111:1989;6661-6666.
13. Griffith D.A., Danishefsky S.J. J. Am. Chem. Soc. 112:1990;5811-5819.
14. Di Bussolo V., Liu J., Huffman L.G. Jr., Gin D.Y. Angew. Chem., Int. Ed. 39:2000;204-207.
15. Liu J., Gin D.Y. J. Am. Chem. Soc. 124:2002;9789-9797.
16. Friesen R.W., Danishefsky S.J. J. Am. Chem. Soc. 111:1989;6656-6660.
17. Ramana C.V., Murali R., Nagarajan M. J. Org. Chem. 62:1997;7694-77703.
18. Hoberg J.O. J. Org. Chem. 62:1997;6615-6618.
19. Hoberg J.O., Bozell J.J. Tetrahedron Lett. 38:1995;6831-6834.
20. Ovaa H., Leeuwenburgh M.A., Overkleeft H. S, van der Marel G.A., van Boom J. Tetrahedron Lett. 39:1998;3025-3028.
21. Rainier J.D., Allwein S.P., Cox J.M. J. Org. Chem. 66:2001;1380-1386.
22. Rainier J.D., Allwein S.P. Tetrahedron Lett. 39:1998;9601-9604.
23. (a) Allwein, S. P.; Cox, J. M.; Howard, B. E.; Johnson, H. W. B.; Rainier, J. D. Tetrahedron, 2002, 58, 1997-2009;
24. (b) Rainier, J. D.; Cox, J. M.; Allwein, S. P. Tetrahedron Lett. 2001, 42, 179-181;
25. (c) Clark, J. S.; Kettle, J. G. Tetrahedron 1999, 55, 8231-8248. In this example the oxepine was not able to be separated from other products of the reaction.
26. (d) Chatterjee, A. K.; Morgan, J. P.; Scholl, M.; Grubbs, R. H. J. Am. Chem. Soc. 2000, 122, 3783-3784;
27. (e) A tandem RCM/olefin isomerization sequence has recently been introduced, see: Sutton, A. E.; Seigal, B. A.; Finnegan, D. F.; Snapper, M. L. J. Am. Chem. Soc. 2002, 124, 13390-13391.
28. Calimente D., Postema M.H.D. J. Org. Chem. 64:1999;1770-1771.
29. Postema M.H.D., Calimente D., Liu F., Berhman T.L. J. Org. Chem. 65:2000;6061-6068.
30. Sturino C.F., Wong C.Y. Tetrahedron Lett. 39:1998;9623-9626.
31. Substituted six and seven membered enol ethers have been synthesized using a tandem methylenation-metathesis approach, see: (a) Nicolaou, K. C.; Postema, M. H. D.; Claiborne, C. F. J. Am. Chem. Soc. 1996, 118, 1565-1566;
32. (b) Nicolaou, K. C.; Postema, M. H. D.; Yue, E. W.; Nadin, A. J. Am. Chem. Soc. 1996, 118, 10335-10336.
33. Martin O.R., Saavedra O.M., Xie F., Liu L., Picasso S., Vogel P., Kizu H., Asano N. Bioorg. Med. Chem. 9:2001;1269-1278.
34. Qioa L., Vederas J.C. J. Org. Chem. 58:1993;3480-3482.
35. Weintraub P.M., King C-H.R. J. Org. Chem. 62:1997;1560-1562.
36. Handerson S., Schlaf M. Org. Lett. 4:2002;407-409.
37. 2 in THF can efficiently mediate cyclization to form the mercuricmethyl C-glycoside, see: Pougny J.R., Nassr M.A.M., Sinaÿ P. J. Chem. Soc., Chem. Commun. 1981;375-376.
38. ++H) calcd 565.2954, found 565.2944.
39. Heating to 60°C or to reflux in toluene in the presence of 20 mol% 9 showed no reaction. Temperature dependence for RCM has been noted elsewhere, see: Majumder, U.; Cox, J. M.; Rainier, J. D. Org. Lett. 2003, 5, 913-916.
40. Schrock R.R. Tetrahedron. 55:1999;8141-8153. and references cited therein.
41. +-H) calcd 535.2484, found 535.2455.
42. Drew K.N. J. Org. Chem. 56:1991;509-513.
43. Wang H., Sun L., Glazebnik S., Zhao K. Tetrahedron Lett. 36:1995;2953-2956.
44. Reed L.A., Ito Y., Masamune S., Sharpless K.B. J. Am. Chem. Soc. 104:1982;6468-6470.
45. Hoye T.R., Zhao H. Org. Lett. 1:1999;1123-1125.
46. Ruthenium-hydrido species of this type are known. See Refs. 13e, 24. We envision the glucal arising from RCM of a truncated diene that comes about by 1,3 hydrogen shift followed by reductive elimination. See also: Miller, S. J.; Blackwell, H. E.; Grubbs, R. H. J. Am. Chem. Soc. 1996, 118, 9606-9614 A similar trunctation using Schrock catalyst has also been reported, see: Joe, D.; Overman, L. E. Tetrahedron Lett. 1997, 38, 8635-8638.
47. Louie J., Grubbs R.H. Organometallics. 21:2002;2153-2164.
48. Sanford M.S., Love J.A., Grubbs R.H. J. Am. Chem. Soc. 123:2001;6453-6554.
49. Grubbs R.H., Chang S. Tetrahedron. 54:1998;4413-4450.
50. Crimmins M.T., Choy A.L. J. Am. Chem. Soc. 121:1999;5653-5660.