Difunctionalised oxirane systems. Stereodivergent synthesis of 1,4;2,3-dianhydro-5-O-benzyl-L-lyxitol and -L-ribitol

Tetrahedron Asymmetry

Volumn 8, Issue 10, 1997, Pages 1611-1621

  Crotti, Paolo ^a   Di Bussolo, Valeria ^a   Favero, Lucilla ^a   Gozzi, Claudia ^a   Pineschi, Mauro ^a  

^a UNIVERSITY OF PISA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

ETHYLENE OXIDE DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CHROMATOGRAPHY; CYCLIZATION; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; STEREOCHEMISTRY;

EID: 0030954187     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(97)00136-5     Document Type: Article

References (32)

1. a) Katsuki, T.; Sharpless, K.B. J. Am. Chem. Soc. 1980, 102, 5974-5976.
2. b) Jacobsen, E.N.; Zhang, W.; Muci, A.R.; Ecker, J.R.; Deng, L. J. Am. Chem. Soc. 1991, 113, 7063-7064, and references therein.
3. Gorzynski Smith, J. Synthesis 1984, 629-656.
4. a) Colombini, M.; Crotti, P.; Di Bussolo, V.; Favero, L.; Gardelli, C.; Macchia, F.; Pineschi, M. Tetrahedron 1995, 57, 8089-8112.
5. b) Chini, M.; Crotti, P.; Gardelli, C.; Macchia, F. J. Org. Chem. 1994, 59, 4131-4137.
6. c) Chini, M.; Crotti, P.; Flippin, L.A.; Gardelli, C.; Giovani, E.; Macchia, F.; Pineschi, M. J. Org. Chem. 1993, 58, 1221-1227.
7. d) Flippin, L.A.; Brown, P.A.; Jalali-Araghi, K. J. Org. Chem. 1989, 54, 3588-3596 and references therein.
8. e) Caron, M; Carlier, P.R.; Sharpless, K.B. J. Org. Chem. 1988, 53, 5185-5187.
9. f) Caron, M.; Sharpless, K.B. J. Org. Chem. 1985, 50, 1557-1560.
10. g) Chong, J.M.; Sharpless, K.B. J. Org. Chem. 1985, 50, 1560-1563.
11. h) Behrens, C.H.; Sharpless, K.B. J. Org. Chem. 1985, 50, 5696-5704.
12. 3 However, due to the easy availability of the starting compound in an enantiopure form [D(+)-xylose], enantiopure epoxides 1 and 2 were more advantageously prepared instead of the racemic ones.
13. The results of the regiochemical behavior of epoxides 1 and 2 together with those of other related oxirane systems will appear in a forthcoming paper.
14. a) Cleophax, J.; Gero, S.D.; Sepulchre, A.M. Acad. Sci. Paris, Ser. C 1968, 267, 162-165.
15. b) Montgomery, J.A.; Thomas, H.J. J. Org. Chem. 1978, 43, 541-544.
16. c) Plavec, J.; Tong, W.; Chattopadhyaya, J. J. Am. Chem. Soc. 1993, 115, 9734-9746.
17. d) Miljkovic, D.A.; Velimirovic, S.S. J. Serb. Chem. Soc. 1988, 53, 31-36.
18. Defaye, J. Bull. Soc. Chim. Fr. 1964, 2686-2689.
19. Corey, E.J.; Erickson, B.W. J. Org. Chem. 1971, 36, 3553-3560.
20. 1H NMR).
21. a) Batten, R.J.; Dixon, A.J.; Taylor, R.J.K. Synthesis 1980, 234-236.
22. b) Greene, T.W.; Wuts, P.G.M. Protective Groups in Organic Synthesis 2nd ed.; Wiley-Interscience, New York, 1991, p 77-83.
23. c) Pilcher, A.S.; Hill, D.K.; Shimshock, S.J.; Waltermire, R.E.; DeShong, P. J. Org. Chem. 1992, 57, 2492-2495.
24. 1H NMR). Succinimide (from NBS) was also present.
25. For example, the reaction of ether 10 with TBAF in THF at - 10°C afforded a 75:25 mixture of alcohols 12 and 13 (see Experimental). Alcohol 13 can be utilized for the synthesis of trans epoxide 2 (Scheme 4).
26. Czernecki, S.; Georgoulis, C.; Provelenghiou, C. Tetrahedron Lett. 1976, 3535-3536.
27. a) Torisawa, Y.; Shibasaki, M.; Ikegami, S. Tetrahedron Lett. 1979, 1865-1868.
28. b) Colvin, E. Silicon in Organic Chemistry, Butterworths; London, 1981, p 187-188.
29. a) Suh, H.; Wilcox, C.S. J. Am. Chem. Soc. 1988, 110, 470-481.
30. b) Nishiyama, S.; Shizuri, Y.; Yamamura, S.; Terada, Y.; Kawai, K.; Furukawa, H. Tetrahedron Lett. 1985, 26, 6239-6242.
31. Zinner, H.; Rembarz, G.; Linke, H.-W.; Ulbricht, G. Chem. Ber. 1957, 90, 1761-1768.
32. Zinner, H.; Brandhoff, H.; Schmandke, H.; Kristen, H.; Haun, R. Chem. Ber. 1959, 92, 3151-3155.