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Synthesis ofD-apio-β-D-furanosyl maleimide, an analogue of showdomycin with transposed hydroxymethyl group

Synthese vonD-Apio-β-D-furanosyl-maleinsäureimid, einem Showdomycinanalogen mit verschobener Hydroxymethylgruppe

  • Organische Chemie Und Biochemie
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Summary

Apioshowdomycin (3-(D-apio-β-D-furanosyl)-1H-pyrrole-2,5-dione,2) has been prepared as an analogue of the C-nucleoside showdomycin (1) in eight steps and with 5% overall yield, starting from 2,3-O-isopropylidene-D-apio-β-D-furanose (3).

Zusammenfassung

Ausgehend von 2,3-O-Isopropyliden-D-apio-β-D-furanose (3) wurde in acht Stufen und 5% Gesamtausbeute Apioshowdomycin (3-(D-Apio-β-D-furanosyl)-1H-pyrrol-2,5-dion,2), ein Analoges des C-Nucleosids Showdomycin (1), hergestellt.

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References

  1. Nishimura H, Mayama M, Komatsu Y, Kato H, Shimaoka N, Tanaka Y (1964) J Antibiot17A: 148

    Google Scholar 

  2. Nakagawa Y, Kano H, Tsukuada Y, Koyama H (1967) Tetrahedron Lett: 4105; Matsuura S, Shiratori O, Katagiri K (1964) J Antibiot17A: 234

  3. Niedzwicki JG, El Kouni MH, Chu SH, Cha S (1983) Biochem Pharmacol32: 399

    Google Scholar 

  4. For reviews on showdomycin see: Suhadolnik RJ (1970) Nucleoside Antibiotics, Wiley-Interscience, New York, Chaps 9 and 10; Suhadolnik RJ (1979) Nucleosides as Biological Probes. Wiley, New York

    Google Scholar 

  5. Barton DHR, Ramesh M (1990) J Am Chem Soc112: 891 and references therein; Barrett AGM, Broughton HB, Attwood SV, Gunatilaka AAL (1986) J Org Chem51: 495 and references therein; Kang SH, Lee SB (1995) J Chem Soc Chem Commun: 1017 and references therein

    Google Scholar 

  6. Mubarak AM, Brown DM (1981) Tetrahedron Lett22: 683; Jung ME, Trifunovich ID, Clevenger GL (1980) J Chem Soc Chem Commun: 84; Jung ME, Clevenger GL (1991) Tetrahedron Lett32: 6089

    Google Scholar 

  7. Mumper MW, Aurenge C, Hosmane RS (1993) Bioorg Med Chem Lett3: 2847; Mumper MW, Aurenge C, Hosmane RS (1994) J Biomol Struct Dyn11: 1107

    Google Scholar 

  8. Jung ME, Trifunovich ID (1992) Tetrahedron Lett33: 2921

    Google Scholar 

  9. Takahashi T, Hironori K, Koizumi T (1992) Nucleic Acids Symp Ser25: 187 (1992) Chem Abstr117: 251697m

    Google Scholar 

  10. Sato T, Noyori R (1983) Bull Chem Soc Jpn56: 2700

    Google Scholar 

  11. Watanabe T, Nishiyama S, Yamamura S, Kato K, Nagai M, Takita T (1991) Tetrahedron Lett32: 2399

    Google Scholar 

  12. Lamberth C, Blarer S (1994) Synlett: 489

  13. Hammerschmidt F, Öhler E, Polsterer J-P, Zbiral E, Balzarini J, DeClercq E (1995) Liebigs Ann Chem: 551

  14. Hammerschmidt F, Öhler E, Polsterer J-P, Zbiral E, Balzarini J, DeClercq E (1995) Liebigs Ann Chem: 559

  15. Hammerschmidt F, Polsterer J-P, Zbiral E (1995) Synthesis: 415

  16. Another approach using the addition of an apiofuranosyl radical to an activated olefin is under progress

  17. For leading references see Ref. [13] and Ref. [14]

  18. Kalvoda L (1976) J Carbohydr Nucleosides Nucleotides3: 47

    Google Scholar 

  19. For the modified protocols and original references see Ref. [13]

  20. Poonian MS, Nowoswiat EF (1980) J Org Chem45: 203; in this work a perbenzoylated ribosyl cyanide was converted to the 1-carboximidic acid methylester by anhydrous work up

    Google Scholar 

  21. Borch RF, Grudinskas CV, Peterson DA, Weber LD (1972) J Org Chem37: 1141

    Google Scholar 

  22. The presence of small quantities of the Zisomer in the crude reaction mixture cannot be excluded

  23. Long range couplings between 1′-H and vinylic hydrogen have also been reported for similar precursors of showdomycin [18]

  24. Tronchet JMJ, Tronchet J (1971) Helv Chim Acta54: 1466; Tronchet JMJ, Tronchet J (1974) Carbohydr Res34: 263

    Google Scholar 

  25. Taylor MD, Moos WH, Hamilton HW, Scotek DS, Patt WC, Badger EW, Bristol JA, Bruns RF, Heffner TG, Mertz TE (1986) J Med Chem29: 346

    Google Scholar 

  26. Mikenda W (1992) Vibrational Spectroscopy3: 327

    Google Scholar 

  27. 2,3-O-Isopropylidene-D-apio-β-D-furanose (3) prepared fromD-mannose according to the protocols given in Ref. [13] occasionally contained up to 15% of the slightly more polar α-anomer and was purified by flash chromatography (hexanes/EtOAc, 7:3) and subsequent crystallization from Et2O/hexanes prior to use

  28. Hettinger P, Schildknecht H (1984) Liebigs Ann Chem: 1230

  29. Kalvoda L (1978) Coll Czech Chem Commun43: 1431

    Google Scholar 

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Authors and Affiliations

  1. Institut für Organische Chemie der Universität Wien, A-1090, Wien, Austria

    F. Hammerschmidt, B. Peric & E. Öhler

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  1. F. Hammerschmidt
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  2. B. Peric
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  3. E. Öhler
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Hammerschmidt, F., Peric, B. & Öhler, E. Synthesis ofD-apio-β-D-furanosyl maleimide, an analogue of showdomycin with transposed hydroxymethyl group. Monatsh Chem 128, 183–190 (1997). https://doi.org/10.1007/BF00807307

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  • DOI: https://doi.org/10.1007/BF00807307

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