Versatile use of bis-cyclic thionocarbonates of polyols as bis-electrophilic intermediates. Synthesis of polyhydroxylated thioanhydropentitols with D,L-arabino, L-ribo and L-xylo, and thioanhydroaldoses with D-lyxo, L-ribo, D-xylo, D-allo, D-gulo and D-altro configurations

Tetrahedron Letters

Volumn 45, Issue 22, 2004, Pages 4365-4369

  Danquigny, Alain ^a   Benazza, Mohammed ^a   Protois, Sylvain ^a   Demailly, Gilles ^a  

^a UNIVERSITÉ DE PICARDIE JULES VERNE   (France)

Author keywords

Alditols; Aldoses dithioacetals; Bis thionocarbonates; Hexoses; Pentoses; Thiaheterocyclisation; Thioanhydro

Indexed keywords

CARBONIC ACID DERIVATIVE; THIOPHENE DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CYCLIZATION; DRUG SYNTHESIS; HETEROCYCLIZATION; HYDROXYLATION; STRUCTURE ANALYSIS;

GULO;

EID: 2342548225     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2004.03.197     Document Type: Article

References (35)

1. Dondoni A., Giovanini P.P., Perrone D. J. Org. Chem. 67:2002;7203-7214
2. Watson A.A., Fleet G.W.J., Asano N., Molyneux R.J., Nash R.J. Phytochemistry. 56:2001;265-295
3. Dondoni A., Merino P., Perrone D. Tetrahedron. 49:1993;2939-2956
4. Fleet G.W.J., Nicholas S.J., Smith P.W., Evans S.W., Fellows L.E., Nasch R.J. Tetrahedron Lett. 26:1985;3127-3130
5. Dyson M.R., Coe P.L., Walker R.T. J. Med. Chem. 34:1991;2782-2786
6. Secrist J.A. III, Tiwari K.N., Riordan J.M., Montgomery J.A. J. Med. Chem. 34:1991;2361-2366
7. Selwood D.V., Carter K., Young R.J., Jandu K.S. Bioorg. Med. Chem. Lett. 8:1996;991-994
8. Tber B., Fahmi N.D., Ronco G., Villa P., Ewing D.F., Mackenzie G. Carbohydr. Res. 267:1995;2203-2216
9. Yoshimura Y., Kitano K., Yamada K., Satoh H., Watanabe M., Miura S., Sakata S., Sasaki T., Matsuda A. J. Org. Chem. 62:1997;3140-3152
10. Yoshimura Y., Watanabe M., Satoh H., Ashida N., Ijichi K., Sakata S., Matchida H., Matsuda A. J. Med. Chem. 40:1997;2177-2183
11. Secrist J.A. III, Tiwari K.N., Shortnacy-Fowler A.T., Messini L., Riordan J.M., Montgomery J.A., Meyers S.C., Ealick S.E. J. Med. Chem. 41:1998;3865-3871
12. Satoh H., Yoshimura Y., Sakata S., Miura S., Machida H. Bioorg. Med. Chem. Lett. 8:1998;989-992
13. Yuasa H., Kajimoto T., Wong C.H. Tetrahedron Lett. 35:1994;8243-8246
14. Yoshikawa M., Murakami T., Shimada H., Matsuda H., Yamahara J., Tanabe G., Muraoka O. Tetrahedron Lett. 38:1997;8367-8370
15. Yoshikawa M., Murakami T., Yashiro K., Matsuda H. Chem. Pharm. Bull. 46:1998;1339-1340
16. Ghavami A., Johnston B.D., Pinto M. J. Org. Chem. 66:2001;2312-2317
17. Ghavami A., Sadalapure K., Johnston B.D., Lobera M., Snider B.B., Pinto M. Synlett. 9:2003;1259-1262
18. Le Merrer Y., Gravier C., Maton W., Numa M., Depezay J.C. Synlett. 8:1999;1322-1324
19. Lohray B.B., Jayamma Y., Chatterjee M. J. Org. Chem. 60:1995;5958-5960
20. Qian X., Varas F.M., Wong C.H. Bioorg. Med. Chem. Lett. 6:1996;1117-1122
21. Halila S., Benazza M., Demailly G. Tetrahedron Lett. 42:2001;3307-3310
22. Kim B.M., Bae S.J., Seomoon G. Tetrahedron Lett. 39:1998;6921-6922
23. Lundt I., Madsen R. Synthesis. 7:1993;714-720
24. Minakawa N., Kato K., Uetake K., Kaga D., Matsuda A. Tetrahedron. 59:2003;1699-1702
25. Esposito A., Falorni M., Taddei M. Tetrahedron Lett. 39:1998;6543-6546
26. Duréault A., Portal M., Depezay J.C. Synlett. 1991;225-226
27. Glaçon V., Benazza M., Beaupère D., Demailly G. Tetrahedron Lett. 41:2000;5053-5056
28. Halila S., Benazza M., Demailly G. Tetrahedron Lett. 43:2002;815-818
29. Cere V., Peri F., Pollicino S. J. Org. Chem. 62:1997;8572-8574
30. Le Merrer Y., Fuzier M., Dosbaa I., Foglietti M.J., Depezay J.C. Tetrahedron. 53:1997;16731-16746
31. Arcelli A., Ceré V., Peri F., Pollicino S., Ricci A. Tetrahedron. 57:2001;3439-3444
32. Unpublished result. The two diastereoisomers were separated by chromatography on silica gel. Further study of this reaction is being undertaken to elucidate the stereochemistry of the sulfoxide and to explain why the allylic hydroxyl group is free and not bearing an ionised sulfate as expected
33. Halila S., Benazza M., Demailly G. J. Carbohydr. Chem. 20:2001;467-483
34. 2-), 127.9-138.6 (Ph-), 138.5-138.6 (C-ipso), 191, 192.8 (C=S)
35. 3), 170.5 (CO)