Sugars containing α,β-unsaturated carbonyl systems: synthesis and their usefulness as scaffolds in carbohydrate chemistry

Carbohydrate Research

Volumn 343, Issue 10-11, 2008, Pages 1523-1539

  Xavier, Nuno M ^a   Rauter, Amélia P ^a  

^a UNIVERSITY OF LISBON   (Portugal)

Author keywords

, Unsaturated carbonyl systems; , Unsaturated pyranuloses; Sugar fused unsaturated lactones; Sugar linked unsaturated ketones; Sugar linked unsaturated lactones

Indexed keywords

BIOACTIVITY; DERIVATIVES; PROTEINS; SCAFFOLDS; SYNTHESIS (CHEMICAL);

CARBONYL SYSTEMS; SUGAR FUSED UNSATURATED LACTONES; SUGAR LINKED UNSATURATED KETONES; SUGAR LINKED UNSATURATED LACTONES;

SUGARS;

1 ENOPYRAN 3 ULOSE DERIVATIVE; 2 ENOPYRANOSID 4 ULOSE DERIVATIVE; 3 ENOPYRANOS 2 ULOSE DERIVATIVE; 4 ENOPYRANOS 3 ULOSE DERIVATIVE; ANTHRACYCLINE ANTIBIOTIC AGENT; ANTIINFECTIVE AGENT; ASCOPYRANONE P; BETA LACTAM ANTIBIOTIC; BUTENOLIDE; C NUCLEOSIDE; CARBOHYDRATE DERIVATIVE; DELTA LACTONE; DIGITOXIN; FURAN DERIVATIVE; GAMMA LACTONE DERIVATIVE; GONIOTHALENOL; KETONE DERIVATIVE; LACTONE DERIVATIVE; PARASORBIC ACID; PATULIN; PYRAN DERIVATIVE; RANUNCULIN; VINEOMYCIN B2;

CARBOHYDRATE ANALYSIS; CARBOHYDRATE SYNTHESIS; DIELS ALDER REACTION; DRUG SYNTHESIS; MICHAEL ADDITION; ONE POT SYNTHESIS; PRIORITY JOURNAL; REVIEW;

4-BUTYROLACTONE; CARBOHYDRATES; FURANS; KETOSES; LACTONES; PYRANS;

EID: 46549088035     PISSN: 00086215     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.carres.2008.04.033     Document Type: Review

References (119)

1. Oh S., Jeong I.H., Shin W.-S., Wang Q., and Lee S. Bioorg. Med. Chem. Lett. 16 (2006) 1656-1659
2. El-Subbagh H.I., Abu-Zaid S.M., Mahran M.A., Badria F.A., and Al-Obaid A.M. J. Med. Chem. 43 (2000) 2915-2921
3. Li D.-H., Zhu T.-J., Liu H.-B., Fang Y.-C., Gu Q.-Q., and Zhu W.-M. Arch. Pharm. Res. 29 (2006) 624-626
4. Cateni F., Zilic J., Zacchigna M., Bonivento P., Frausin F., and Scarcia V. Eur. J. Med. Chem. 41 (2006) 192-200
5. Anke T., Watson W., Giannetti B., and Steglich W. J. Antibiot. 34 (1981) 1271-1277
6. Husain A., Hasan S.M., Lal S., and Alam M.M. Indian J. Pharm. Sci. 68 (2006) 536-538
7. Maria A.O.M., Donadel O., Wendel G.H., Guzman J.A., Guerreiro E., and Giordano O.S. Biol. Pharm. Bull. 23 (2000) 555-557
8. Favier L.S., Maria A.O.M., Wendel G.H., Borkowski E.J., Giordano O.S., Pelzer L., and Tonn C.E. J. Ethnopharmacol. 100 (2005) 260-267
9. Rungeler P., Castro V., Mora G., Goren N., Vichnewski W., Pahl H.L., Merfort I., and Schmidt T. J. Bioorg. Med. Chem. 7 (1999) 2343-2352
10. For reviews concerning the synthesis and biological properties of α,β-unsaturated lactones, see:. Marco J.A., Carda M., Murga J., and Falomir E. Tetrahedron 63 (2007) 2929-2958
11. Boucard V., Broustal G., and Campagne J.M. Eur. J. Org. Chem. (2007) 225-236
12. Bruckner R. Curr. Org. Chem. 5 (2001) 679-718
13. Knight D.W. Contemp. Org. Synth. 1 (1994) 287-315
14. Rao Y.S. Chem. Rev. 76 (1976) 625-694
15. Zhou M., and O'Doherty G.A. J. Org. Chem. 72 (2007) 2485-2493
16. Greeff K. Cardiac Glycosides, Part 1: Experimental Pharmacology. Handbook of Experimental Pharmacology Vol. 56 (1981), Springer, Berlin, New York
17. Honma M., and Nakada M. Tetrahedron Lett. 48 (2007) 1541-1544
18. Haux J. Med. Hypotheses 53 (1999) 543-548
19. Kometiani P., Liu L., and Askari A. Mol. Pharmacol. 67 (2005) 929-936
20. Lopez-Lazaro M., Pastor N., Azrak S.S., Ayuso M.J., Austin C.A., and Cortes F. J. Nat. Prod. 68 (2005) 1642-1645
21. Winnicka K., Bielawski K., and Bielawska A. Acta Pol. Pharm. 63 (2006) 109-115
22. For a review of cardiotonic steroids see:. Melero C.P., Medarde M., and San Feliciano A. Molecules 5 (2000) 51-81
23. Camps P., Cardellach J., Font J., Ortuño R.M., and Pansati O. Tetrahedron 38 (1982) 2395-2402
24. Cottier L., Descotes G., and Soro Y. J. Carbohydr. Chem. 24 (2005) 55-71
25. Bennet M., Gill G.B., Pattenden G., Shuker A.J., and Stapleton A. J. Chem. Soc., Perkin Trans. 1 1991 (1991) 929-937
26. Rychlik M., and Schieberle P. J. Agric. Food Chem. 46 (1998) 5163-5169 and references cited herein
27. Liu H.-M., Zhang F., Zhang J., and Shi L. Carbohydr. Res. 338 (2003) 1737-1743
28. Xavier N.M., and Rauter A.P. Org. Lett. 9 (2007) 3339-3341
29. Goddard-Borger E.D., Ghisalberti E.L., and Stick R.V. Eur. J. Org. Chem. 23 (2007) 3925-3934
30. Rauter A.P., Figueiredo J.A., Ismael M.I., Pais M.S., Gonzalez A.G., Dias J., and Barrera J.B. J. Carbohydr. Chem. 6 (1987) 259-272
31. Rauter A.P., Ferreira M.J., Font J., Virgili A., Figueredo M., Figueiredo J.A., Ismael M.I., and Canda T.L. J. Carbohydr. Chem. 14 (1995) 929-948
32. Rauter A.P., Figueiredo J., Ismael M., Canda T., Font J., and Figueredo M. Tetrahedron: Asymetry 12 (2001) 1131-1146
33. Justino J., Rauter A.P., Canda T., Wilkins R., and Matthews E. Pest. Manage. Sci. 61 (2005) 985-990
34. Gosh A.K., Cappiello J., and Shin D. Tetrahedron Lett. 39 (1998) 4651-4654
35. El Sukkari H., Gesson J.-P., and Renoux B. Tetrahedron Lett. 39 (1998) 4043-4046
36. Radha Krishna P., and Narsingam M. J. Comb. Chem. 9 (2007) 62-69
37. Sharma G.V.M., Rajendra Prasad T., Radah Krishna P., Ramana Rao M.H.V., and Kunwar A.C. J. Carbohydr. Chem. 21 (2002) 501-511
38. Maeba I., Suzuki M., Hara O., Takeuchi T., Iijima T., and Furukawa H. J. Org. Chem. 52 (1987) 4521-4526
39. Gesson J.-P., Jacquesy J.-C., and Mondon M. Tetrahedron 45 (1989) 2627-2640
40. Recent references on the synthesis of altholactone:. Prasad K.R., and Gholap S.L. J. Org. Chem. 73 (2008) 2-11 and references cited herein
41. Yadav J.S., Rajaiah G., and Raju A.K. Tetrahedron Lett. 44 (2003) 5831-5833 and references cited herein
42. Isolation of altholactone:. Loder J.W., and Nearn R.H. Heterocycles 7 (1977) 113
43. El-Zayat A.E., Ferrigni N.R., McCloud T.G., McKenzie A.T., Byrn S.R., Cassady J.M., Chang C., and McLaughlin J.L. Tetrahedron Lett. 26 (1985) 955-956
44. Patil N.T., Tilekar J.N., and Dhavale D.D. J. Org. Chem. 66 (2001) 1065-1074
45. Sharma G.V.M., and Radah Krishna P. Curr. Org. Chem. 8 (2004) 1187-1209
46. Sharma G.V.M., Begum A.K., Kumar R., Rada Krishna P., Prabhakar A., and Kunwar A.C. Tetrahedron Lett. 46 (2005) 4131-4135
47. Stephens B.E., and Liu F. Tetrahedron Lett. 48 (2007) 9116-9119
48. Jarglis P., and Lichtenthaler F.W. Tetrahedron Lett. 23 (1982) 3781-3784
49. Lichtenthaler F.W., Klingler F.D., and Jarglis P. Carbohydr. Res. 132 (1984) C1-C4
50. Lichtenthaler F.W., and Werner B. Carbohydr. Res. 319 (1999) 47-54
51. Fehlhaber H.-W., Snatzke G., and Vlahov I. Liebigs Ann. Chem. (1987) 637-638
52. Mostowicz D., Jurczak M., Hamann H.-J., Höft E., and Chmielewski M. Eur. J. Org. Chem. (1998) 2617-2621
53. Panfil I., Mostowicz D., and Chmielewski M. Polish J. Chem. 73 (1999) 1099-1110
54. Hamann H.-J., Höft E., Mostowicz D., Mishnev A., Urbañczyk-Lipkowska Z., and Chmielewski M. Tetrahedron 53 (1997) 185-192
55. Rollin P., and Sinay P. Carbohydr. Res. 98 (1981) 139-142
56. Bonadies F., Di Fabio R., and Bonini C. J. Org. Chem. 49 (1984) 1647-1649
57. Rauter A.P., Canda T., Justino J., Ismael M.I., and Figueiredo J.A. J. Carbohydr. Chem. 23 (2004) 239-251
58. Yadav J.S., Subba Reddy B.V., and Suresh Reddy C. Tetrahedron Lett. 45 (2004) 4583-4585
59. Panfil I., Mostowicz D., and Chmielewski M. Polish J. Chem. 73 (1999) 1099-1110
60. Panfil I., Urbañczyk-Lipkowska Z., Suwiñka K., Solecka J., and Chmielewski M. Tetrahedron 58 (2002) 1199-1212
61. Jurczak M., Rabiczko J., Socha D., Chmielewski M., Cardona F., Goti A., and Brandi A. Tetrahedron: Asymmetry 11 (2000) 2015-2022
62. Sasaki K., Matsumura S., and Toshima K. Tetrahedron Lett. 48 (2007) 6982-6986 and references cited herein
63. Andreassen M., and Lundt I. Carbohydr. Res. 341 (2006) 1692-1696 and references cited herein
64. Sharma G.V.M., Hymavathi L., and Radha Krishna P. Tetrahedron Lett. 38 (1997) 6929-6932
65. Sharma G.V.M., Subhash Chander A.S., Rada Krishna P., Krishnudu K., Ramana Rao M.H.V., and Kunwar A.C. Tetrahedron: Asymmetry 11 (2000) 2643-2646
66. Holder N.L. Chem. Rev. 82 (1982) 287-332
67. Lichtenthaler F.W. Pure Appl. Chem. 50 (1978) 1343-1362
68. Czernecki S., Vijayakumaran K., and Ville G. J. Org. Chem. 51 (1986) 5472-5475
69. Compound 70 was synthesized by the same procedure as precursor for the synthesis of l-digitoxose, although with a different work-up than that described in Ref. 35a, see:. Timmons S.C., and Jakeman D.L. Carbohydr. Res. 342 (2007) 2695-2704
70. Bellosta V., Benhaddou R., and Czernecki S. Synlett (1993) 861-863
71. Hayashi M., Yamada K., and Aridita O. Tetrahedron Lett. 40 (1999) 1171-1174
72. Hayashi M., Yamada K., and Arikita O. Tetrahedron 55 (1999) 8331-8340
73. Benhaddou R., Czernecki S., and Ville G. J. Org. Chem. 57 (1992) 4612-4616
74. Hayashi M., Kawabata H., Shimono S., and Kakehi A. Tetrahedron Lett. 41 (2000) 2591-2594
75. Kirschning A., Drager G., and Harders J. Synlett (1993) 289
76. Kirschning A. J. Org. Chem. 60 (1995) 1228-1232
77. Gardiner J.M., Mills R., and Fessard T. Tetrahedron Lett. 45 (2004) 1215-1217
78. Danishefsky S., Kerwin Jr. J.F., and Kobayashi S. J. Am. Chem. Soc. 104 (1982) 358-360
79. Danishefsky S., Kato N., Askin D., and Kerwin Jr. J.F. J. Am. Chem. Soc. 104 (1982) 360-362
80. Danishefsky S., Kobayashi S., and Kerwin Jr. J.F. J. Org. Chem. 47 (1982) 1981-1983
81. Michael K., and Kessler H. Tetrahedron Lett. 37 (1996) 3453-3456 and references cited herein
82. Ganguly D., Tang H., and Rodriguez M.J. Synth. Commun. 37 (2007) 4219-4226
83. Kirschning A., and Harders J. Tetrahedron 53 (1997) 7867-7876 and references cited herein
84. Goodwin T.E., Rothman N.M., Salazar K.L., and Sorrels S.L. J. Org. Chem. 57 (1992) 2469-2471
85. Leonelli F., Capuzzi M., Calcagno V., Passacantilli P., and Piancatelli G. Eur. J. Org. Chem. (2005) 2671-2676
86. Achmatowicz O., and Szechner B. Tetrahedron 53 (1997) 6035-6044
87. Prevost N., and Rouessac F. Synth. Commun. 27 (1997) 2325-2335
88. Witczak Z.J., Chen H., and Kaplon P. Tetrahedron: Asymmetry 11 (2000) 519-532
89. Horton D., Roski J.P., and Norris P. J. Org. Chem. 61 (1996) 3783-3793
90. de Freitas Filho R.J., Srivastava R.M., da Silva W.J.P., Cottier L., and Sinou D. Carbohydr. Res. 338 (2003) 673-680
91. Ferrier R.J., and Prasad N. J. Chem. Soc. C (1969) 570-575
92. Sagar R., Pant C.S., Pathak R., and Shaw A.K. Tetrahedron 60 (2004) 11399-11406
93. Morita K., Suzuki Z., and Hirose H. Bull. Chem. Soc. Jpn. 41 (1968) 2815-2816
94. Baylis, A. B.; Hillman, M. E. D. German Patent 2155113, 1972; Chem. Abstr. 1972, 77, 34174q.
95. Samet A.V., Shestopalov A.M., Lutov D.N., Rodinovskaya L.A., Shestopalov A.A., and Semenov V.V. Tetrahedron: Asymmetry 18 (2007) 1986-1989 and references cited herein
96. Taniguchi T., Nakamura K., and Ogasawara K. Synlett (1996) 971-972
97. Taniguchi T., Nakamura K., and Ogasawara K. J. Chem. Soc., Chem. Commun. (1996) 1477-1478
98. De Fina G.M., Varela O., and Lederkremer R.M. Synthesis (1988) 891-893
99. Iriarte Capaccio C.A., and Varela O. J. Org. Chem. 66 (2001) 8859-8866
100. Iriarte Capaccio C.A., and Varela O. J. Org. Chem. 67 (2002) 7839-7846
101. Valera O., de Fina G.M., and de Lederkremer R.M. Carbohydr. Res. 167 (1987) 187-196
102. Uhrig M.L., and Varela O. Synthesis (2005) 893-898
103. Herscovici J., Boumaiza L., and Antonakis K. J. Org. Chem. 57 (1992) 2476-2480
104. Herscovici J., Delatre S., and Antonakis K. J. Org. Chem. 52 (1987) 5691
105. Collins P.M., Overand W.G., and Rayner B.A. Carbohydr. Res. 31 (1973) 1-16
106. Lichtenthaler F.W., Strobel K., and Reidel G. Carbohydr. Res. 49 (1976) 57-67
107. Mackie D.M., and Perlin A.S. Carbohydr. Res. 24 (1972) 67-85
108. Uhrig M.L., and Varela O. Aust. J. Chem. 55 (2002) 155-160
109. Uhrig M.L., and Varela O. Carbohydr. Res. 337 (2002) 2069-2076
110. Ruiz R.M., Martinéz I.O., Michalik M., Reinke H., Suarez J.Q., and Peseke K. J. Carbohydr. Chem. 23 (2004) 337-351
111. Samet A.V., Niyazymbetov M.E., and Semenov V.V. J. Org. Chem. 61 (1996) 8786-8791
112. Witczak Z.J., Sun J., and Mielguj R. Bioorg. Med. Chem. Lett. 5 (1995) 2169-2174
113. Witczak Z.J., Chhabra R., Chen H., and Xie X.-Q. Carbohydr. Res. 301 (1997) 167-175
114. Becker B., Thimm J., and Thiem J. J. Carbohydr. Chem. 15 (1996) 1179-1181
115. Uhrig M.L., Manzano V.E., and Varela O. Eur. J. Org. Chem. (2006) 162-168
116. Uhrig M.L., Szilágyi L., Kover K.E., and Varela O. Carbohydr. Res. 342 (2007) 1841-1849
117. Iriarte Capaccio C.A., and Varela O. Tetrahedron: Asymmetry 15 (2004) 3023-3028
118. Iriarte Capaccio C.A., and Varela O. Carbohydr. Res. 340 (2005) 2104-2110
119. Witczak Z.J., Lorchak D., and Nguyen N. Carbohydr. Res. 342 (2007) 1929-1933