Abstract
Anhydro sugars have proved to be versatile chiral synthons for the synthesis of chiral heterocycles including pyradazines, oxazines, triazines, chiral morpholines, tetrahydroquinoxalines, benzodioxins, oxazolidinones, episulfides, thiazolines, and cyclic trithiocarbonates. Selected examples are described in this chapter.
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References
Vethaviyasar N, Kimmich R, Voelter W (1977) Chem Ztg 101:36
Kimmich R, Voelter W (1981) Liebigs Ann Chem, p 1100
Afza N, Malik A, Voelter W (1983) Chimia 37:422
Malik A, Kowollik W, Scheer P, Afza N, Voelter W (1984) J Chem Soc Chem Commun, p 1229
Malik A, Afza N, Roosz M, Voelter W (1984) J Chem Soc Chem Commun, p 1530
Malik A, Roosz M, Voelter W (1985) Z Naturforsch 40b:559
Kowollik W, Malik A, Afza N, Voelter W (1985) J Org Chem 50:3325
Afza N, Malik A, Latif F, Voelter W (1985) Liebigs Ann Chem, p 1929
Latif F, Malik A, Voelter W (1987) Liebigs Ann Chem, p 717
Kowollik W, Janairo G, Voelter W (1988) Liebigs Ann Chem, p 427
Kowollik W, Voelter W (1988) Liebigs Ann Chem, p 433
Shekhani MS, Latif F, Fatima A, Malik A, Voelter W (1988) J Chem Soc Chem Commun, p 1419
Kowollik W, Janairo G, Voelter W (1988) J Org Chem 53:3943
Fatima A, Zaman F, Shekhani MS, Malik A, Voelter W (1990) Liebigs Ann Chem, p 389
Latif F, Shekhani MS, Voelter W (1990) J Chem Soc Perkin Trans 1, p 1573
Kowollik W, Voelter W (1992) Z Naturforsch 47b:589
Al-Tel TH, Al-Abed Y, Shekhani MS, Voelter W (1993) Tetrahedron Lett 34:7717
Al-Abed Y, Al-Tel TH, Voelter W (1993) Tetrahedron 49:9295
Al-Abed Y, Al-Tel TH, Voelter W (1994) Nat Prod Lett 4:273
Al-Tel TH, Al-Abed Y, Voelter W (1994) J Chem Soc Chem Commun, p 1735
Kazmi SN, Ahmed Z, Malik A, Afza N, Voelter W (1994) Z Naturforsch 50b:294
Tschakert J, Voelter W (1994) Z Naturforsch 49b:702
Zaman F, Fatima A, Malik A, Voelter W (1994) Z Naturforsch 49b:1434
Al-Tel TH, Al-Qawasmeh RA, Schröder C, Voelter W (1995) Tetrahedron 51:3141
Abu Zarga MH, Al-Tel TH, Voelter W (1995) Z Naturforsch 50b:697
Al-Tel TH, Voelter W (1995) Tetrahedron Lett 36:523
Al-Tel TH, Al-Qawasmeh RA, Kaiser T, Voelter W (1995) Tetrahedron Lett 36:4599
Al-Tel TH, Meisenbach M, Voelter W (1995) Liebigs Ann Chem, p 689
Stang PJ, Hanack M, Subramanian LR (1982) Synthesis, p 85
Binkley RW, Ambrose MG (1984) J Carbohydr Chem 3:1
Rosowski A (1964) In: Weissberger A (ed) Heterocyclic compounds with three- and four-membered rings, part III. Interscience, New York
Baldwin JE, Kruse LI (1977) J Chem Soc Chem Commun, p 233
Al-Tel TH, Al-Abed Y Voelter W (1995) J Chem Soc Chem Commun, p 239
Baldwin JE, Lusch MJ (1982) Tetrahedron 38:2939
Al-Qawasmeh RA, Al-Tel TH, Abdel-Jalil RJ, Thürmer R, Voelter W (1999) Polish J Chem 73:71
Al-Abed Y, Voelter W (1997) GIT Labor-Fachzeitschrift, special edition 58–61
Al-Abed Y, Zaman F, Shekhani MS, Fatima A, Voelter W (1992) Tetrahedron Lett 33:3305
Grieco PA, Miyashita M (1974) J Org Chem 39:120
Al-Abed Y, Naz N, Mooto D, Voelter W (1996) Tetrahedron Lett 37:8641
Honda T, Kobayashi Y, Tsubuki M (1993) Tetrahedron 49:1211
Al-Qawasmeh RA, Al-Tel TH, Abdel-Jalil RJ, Voelter W (1999) Chem Lett, p 541
Rong J, Roselt P, Plavec J, Chattopadhyaya J (1994) Tetrahedron 50:4921
Hossain N, Papchikhin A, Plavec J, Chattopadhyaya J (1993) Tetrahedron 49:10133
Papchikhin A, Chattopadhyaya J (1994) Tetrahedron 50:5279
Papchikhin A, Agback P, Plavec J, Chattopadhyaya J (1993) J Org Chem 58:2874
Pan S, Amankulor N, Zhao K (1998) Tetrahedron 54:6587
Mann J, Thomas A (1985) J Chem Soc Chem Commun, p 737
Mancera M, Roffé I, Galbis JA (1995) Tetrahedron 51:6349
Saeed M, Abdel-Jalil RJ, Voelter W, El-Abadelah MM (2001) Chem Lett, p 660
Trepanier DL (1967) US Patent 3510483
Trepanier DL (1970) Chem Abstr 73:35415y
El-Abadelah MM, Hussein AQ, Thaher BA (1991) Heterocycles 32:1879
Butler RN, Scott FL (1970) Chem Ind (London) 1216
Abdel-Jalil RJ, Shah STA, Khan KM, Voelter W (2005) Lett Org Chem 2:306
Gupta K, Sauder DN, Shear NH (1994) J Am Acad Dermatol 30:911
Grieco G, DeAndrade J, Dorflinger E, Kantor T, Saelens J, Sunshine A, Wang R, Wideman G, Zellman V (1989) Clin Pharmacol Ther 45:123
Brogdan RN, Speight TM, Avery GS (1975) Drugs 9:164
Liu M-C, Lin T-S, Penketh P, Sartorelli AC (1995) J Med Chem 38:4234
Acton EM, Tong GL, Mosher CW, Wolgemuth RL (1984) J Med Chem 27:638
Özarslan Ö, Ertan M, Sayrac T, Akgün H, Demirdamar R, Gümüsel B (1994) Arch Pharm 327:525
Ambra TED, Estep KG, Bell MR, Eissenstat MA, Josef KA, Ward SJ, Haycock LA, Baizman ER, Casiano FM, Beglin NC, Chippari SM, Grego JD, Kullnig RK, Daley GT (1992) J Med Chem 35:124
Kato S, Morie T, Kon T, Yoshida N, Karasawa T, Matsumoto J-I (1991) J Med Chem 34:616
Dewald HA, Heffner TG, Jaen JC, Lustgarten DM, McPhaill AT, Meltzer LT, Pugsley TA, Wiese LD (1990) J Med Chem 33:445
Nozulak J, Vigouret JM, Jaton AL, Hofmann A, Dravid AR, Weber HP, Kalkman HO, Walkinshaw MD (1992) J Med Chem 35:480
Tani E, Rekka E, Kourounakis PN (1994) Arzneim Forsch/Drug Res 44:992
Bartroli J, Turmo E, Alguero M, Boncompte E, Vericat ML, Rafanell-García J, Forn J (1995) J Med Chem 38:3918
Abdel-Jalil RJ, Shah STA, Khan KM, Voelter W (2005) Lett Org Chem 2:238
Forlani L, Medici A, Ricci M, Todesco PE (1997) Synthesis, p 230
Boido A, Vazzana I, Sparatore F (1994) Farmaco 49:97
Monge A, Palop JA, de Cerain AL, Senaedor V, Martinez-Crespo FJ, Sainz Y, Narro S, Garica E, de Miguel C, Gonzalez M, Hamilton E, Barker AJ, Clarke ED, Greenhow DT (1995) J Med Chem 38:1786
Glombic H (1990) Offen. DE Patent 3826603
Glombic H (1990) Chem Abstr 113:9762w
Loev B, Musser JH, Brown RE, Jones H, Kahen R, Huang FC, Khandwala A, Sonnino-Goldmann P, Leibowitz MJ (1985) J Med Chem 28:363
Khandwala A, Inwegen RV, Coutts S, Dally-meade V, Jariwala N, Huang F, Musser J, Brown R, Loev B, Weinryb I (1984) Int Arch Allergy Appl Immunol 73:56
Khandwala A, Inwegen RV, Coutts S, Dally-meade V, Jariwala N, Huang F, Musser J, Brown R, Loev B, Weinryb I (1984) Chem Abstr 100:185318j
Kim KS Qian L, Bird JE, Dickinson KEJ, Moreland S, Schaeffer TR, Waldron TL, Delaney CL, Weller HN, Miller AV (1993) J Med Chem 36:2335
Catarzi D, Cecchi L, Colotta V, Filacchioni G, Martini C, Tacchi P, Lucacchini A (1995) J Med Chem 38:1330
Catarzi D, Cecchi L, Colotta V, Melani F, Filacchioni G, Martini C, Giusti A, Lucacchini A (1994) J Med Chem 37:2846
Shin-ya K, Furihata K, Hayakawa Y, Kato Y, Clardy J (1991) Tetrahedron Lett 32:943
Salituro FG, Harrison BL, Maron BM, Nyce PL, Stewart KT, McDonald IA (1990) J Med Chem 33:2946
Chapleo CB, Myers PL, Butler RCM, Doxey JC, Roach AG, Smith CFM (1983) J Med Chem 26:823
Hibert MF, Gittos MW, Middlemiss DN, Mir AK, Fozard JR (1988) J Med Chem 31:1087
Werner LH, Barnatt WW (1967) In: Schlitter E (ed) Antihypertensive agents. Academic, New York
Fourneau E, Bovet D, Maderni P (1933) J Pharm Clin 18:185
Fourneau E, Bovet D (1933) CR Seances Soc Biol Fil 113:388
Baker BR (1964) J Org Chem 29:1057
Inghardt T, Frejd T, Magnusson G (1988) J Org Chem 53:4542
Kowollik W (1987) PhD thesis, Tübingen University, Germany
Trost BM, Van Vranken DL, Bingel C (1992) J Am Chem Soc 114:9327
Gordon DM, Danishifsky SJ (1991) J Am Chem Soc 56:3713
Goodman L, Christensen JE (1961) J Am Chem Soc 83:3823
Goodman L, Christensen JE (1961) J Am Chem Soc 83:3827
Barker BR, Hullar TL (1965) J Org Chem 30:4038
Voelter W, Al-Tel TH, Al-Abed Y, Khan N, Al-Qawasmeh RA, Thürmer R (1998) In: Atta-ur-Rahman, Choudhary MI (eds) New trends in natural product chemistry. Harwood Academic, pp 47–56
Saeed M, Abbas M, Abdel-Jalil RJ, Zahid M, Voelter W (2003) Tetrahedron Lett 44:315
Sundin A, Frejd T, Magnusson G (1986) J Org Chem 51:3927
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Khan, K.M., Perveen, S., Voelter, W. (2007). Anhydro Sugars: Useful Tools for Chiral Syntheses of Heterocycles. In: El Ashry, E.S.H. (eds) Heterocycles from Carbohydrate Precursors. Topics in Heterocyclic Chemistry, vol 7. Springer, Berlin, Heidelberg. https://doi.org/10.1007/7081_2007_078
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DOI: https://doi.org/10.1007/7081_2007_078
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