Synthesis of diastereoisomeric 6-deoxy-d-allal- and 6-deoxy-d-galactal-derived allyl epoxides and examination of the regio- and stereoselectivity in nucleophilic addition reactions. Comparison with the corresponding 6-O-functionalized allyl epoxides

Tetrahedron

Volumn 64, Issue 35, 2008, Pages 8188-8201

  Di Bussolo, Valeria ^a   Favero, Lucilla ^a   Romano, Maria Rosaria ^a   Pineschi, Mauro ^a   Crotti, Paolo ^a  

^a UNIVERSITY OF PISA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL; EPOXIDE; MONOSACCHARIDE;

ADDITION REACTION; ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CIS ISOMER; CYCLIZATION; DESILYLATION; DIASTEREOISOMER; GLYCOSYLATION; PRIORITY JOURNAL; STEREOCHEMISTRY; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 47049107011     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2008.06.039     Document Type: Article

References (50)

1. Di Bussolo V., Caselli M., Pineschi M., and Crotti P. Org. Lett. 4 (2002) 3695-3698
2. Org. Lett. 5 (2003) 2173-2176
3. Di Bussolo V., Caselli M., Romano M.R., Pineschi M., and Crotti P. J. Org. Chem. 69 (2004) 7383-7386
4. J. Org. Chem. 69 (2004) 8702-8708
5. 3d
6. Clive D.L.J., Tao Y., Bo Y., Hu Y.-Z., Selvakumar N., Sun S., Daigneault S., and Wu Y.-J. Chem. Commun. (2000) 1341-1350
7. Knapp S., Lal G.S., and Sahai D. J. Org. Chem. 51 (1986) 380-383
8. Yunker M.B., Tam S.Y.-K., Hicks D.R., and Fraser-Reid B. Can. J. Chem. 54 (1976) 2411-2416
9. Bueno J.M., Coterón J.M., Chiara J.L., Fernández-Mayoralas A., Fiandor J.M., and Valle N. Tetrahedron Lett. 41 (2000) 4379-4382
10. Di Bussolo V., Favero L., Macchia F., Pineschi M., and Crotti P. Tetrahedron 58 (2002) 6069-6091
11. Fraser-Reid B., Kelly D.R., Tulshian D.B., and Ravi P.S. J. Carbohydr. Chem. 2 (1983) 105-114
12. Pihko A.J., Nicolaou K.C., and Koskinen A.M.P. Tetrahedron: Asymmetry 12 (2001) 937-942
13. Epoxides 8α and 8β are not isolable, and can only be prepared in situ by cyclization of the corresponding stable precursors, the trans-hydroxy mesylates 17 and 21, respectively, and left immediately to react with a nucleophile.
14. For a recently described synthesis of 6-deoxy-d-gulal (18), see:. Engstrom K.M., Mendoza M.R., Navarro-Villalobos M., and Gin D.Y. Angew. Chem., Int. Ed. 40 (2001) 1128-1130
15. -). In this reaction, contrary to expectations, trans-diol 18 was the only reaction product: a saponification process on the primary reaction product, the monoacetate 18-Ac, reasonably occurred under the slightly alkaline reaction conditions (Scheme 3).
16. It is interesting to note that the unique (1β′-OMe, 1β′, 1β′-Tr and 8β′) and the more stable conformer (1α′-OMe, 1α′ and 8α′) present at the equilibrium in epoxides 1β-OMe, 1β, 1β-Tr, 8β, 1α-OMe, 1α and 8α contain the same ring conformation, with the oxirane and the endocyclic oxygen on the same side of the molecular plane. Corresponding conformers 1β″-OMe, 1β″, 1β″-Tr and 8β″ (not present) and 1α″-OMe, 1α″ and 8α″ (less stable) have the two oxygens on the opposite side of the molecular plane. All the results obtained in this theoretical conformational study are the subject of a manuscript from our laboratory: Crotti, P.; Di Bussolo, V.; Pomelli, C. S.; Favero, L. Theor. Chem. Acc., submitted for publication.
17. 2O, MeCN or THF) was treated with t-BuOK (1 equiv). After the TLC analysis showed that the starting material was completely consumed (15-30 min), the glycosyl acceptor (O-, C-, N- or S-nucleophile, 3-4 equiv) was added.
18. 1a,b,d
19. Achmatowicz Jr. O., and Szechner B. Carbohydr. Res. 50 (1976) 23-33 See also:
20. Achmatowicz Jr. O., Bukowski P., Szechner B., Zwierzchowska Z., and Zamojski A. Tetrahedron 27 (1971) 1973-1996
21. Ramnauth J., Poulin O., Rakhit S., and Maddaford S.P. Org. Lett. 3 (2001) 2013-2015
22. Hayashi M., Kawabata H., and Nakayama S.-Z. Chirality 15 (2003) 10-16
23. Pudlo P., Thiem J., and Vill V. Chem. Ber. 123 (1990) 1129-1135
24. The proposed oxirane oxygen-nucleophile coordination appears at the moment as the only rationalization able to justify the regio- and stereoselectivity obtained both with coordinating and non-coordinating nucleophiles. However, at least in principle, the occurrence of other effects cannot be ruled out.
25. 1d
26. Shenoy S.R., Smith D.M., and Woerpel K.A. J. Am. Chem. Soc. 128 (2006) 8671-8677 and references therein
27. Among the four diastereoisomeric 6-deoxy azido alcohols, cis-azido alcohol 50 has not been previously described.
28. For the 4-OBz derivative of the enantiomer of 48β, see:. Kirschning A., Domann S., Dräger G., and Rose L. Synlett (1995) 767-769.
29. For the 4-OAc or 4-OBz derivative of 54, 56, 60 and 62, see:
30. Boivin J., Montagnac A., Monneret C., and Pais M. Carbohydr. Res. 85 (1980) 223-242
31. Boivin J., Pais M., and Monneret C. Carbohydr. Res. 79 (1980) 193-204
32. 1d
33. 3): after two days 55-Ac/53α-Ac=67:33.
34. The syn-1,2-addition product (56)/coordination product (54α-OTMS) ratio increased from about 1.25:1 after 10 min to about 5.3:1 after 30 min.
35. For examples of [3,3]-sigmatropic rearrangement by the azido group, see:
36. Heyns K., and Hohlweg R. Chem. Ber. 111 (1978) 1632-1645
37. Paulsen H., and Heiker F.R. Carbohydr. Res. 102 (1982) 83-98
38. Takasu H., Tsuji Y., Sajiki H., and Hirota K. Tetrahedron 61 (2005) 11027-11031
39. 1H NMR analysis indicated only the presence of trans-azido alcohol 61 (85%) and cis-azido alcohol 55 (15%).
40. Bonner O.D. J. Phys. Chem. 83 (1979) 1218-1220
41. Moss R.A., Terpinski J., Cox D.P., Denny D.Z., and Krogh-Jespersen K. J. Am. Chem. Soc. 107 (1985) 2743-2748
42. 1d
43. 8, respectively, the same attack in 1β-Tr and 8β corresponds to a less favourable pseudoequatorial attack (structure 71b, route b, Scheme 14, where only epoxide 8β is shown), thus justifying the smaller amount of 1,4-addition product obtained in the reaction of these allyl β oxirane systems with S-nucleophiles.
44. Sabesan S., and Neira S. Carbohydr. Res. 223 (1992) 169-185
45. Priebe W., and Zamojski A. Tetrahedron 36 (1980) 287-297
46. Halcomb R.L., Wittman M.D., Olson S.H., Danishefsky S.J., Golik J., Wong H., and Vyas D. J. Am. Chem. Soc. 113 (1991) 5080-5082
47. Wittman M.D., Halcomb R.L., Danishefsky S.J., Golik J., and Vyas D. J. Org. Chem. 55 (1990) 1979-1981
48. Dunkerton L.V., Adair N.K., Euske J.M., Brady K.T., and Robinson P.D. J. Org. Chem. 53 (1988) 845-850
49. Stothers J.B. Carbon-13 NMR Spectroscopy (1973), Academic, New York, NY Chapter 3
50. Orsini F., and Pelizzoni F. Carbohydr. Res. 243 (1993) 183-189