An Expedient Asymmetric Synthesis of a Calystegine B₄ Analogue

Abstract

A convenient, high-yielding synthetic route to polyhydroxylated 6-oxa-nor-tropanes that mimic the structural framework of calystegine B₄ is reported.

Key words

alkaloids - glycosidase inhibitors - piperidines - asymmetric synthesis - calystegines

References

• 1 Asano N. Nash RJ. Molyneux RJ. Fleet GWJ. Tetrahedron: Asymmetry  2000,  11:  1645 
• For recent reviews on this subject see:
• 2a Zechel DL. Withers SG. Acc. Chem. Res.  2000,  33:  11 
• 2b Stütz AE. In Iminosugars as Glycosidase Inhibitors: Nojirimycin and Beyond   Wiley-VCH; Weinheim: 1999. 
• 2c Heightman TD. Vasella AT. Angew. Chem., Int. Ed.  1999,  38:  750 
• 3a Holman RR. Cull CA. Turner RC. Diabetes Care  1999,  22:  960 
• 3b Platt FM. Neises GR. Reinkensmeir G. Townsend MJ. Perry VH. Proia RL. Winchester B. Dwek RA. Butters TD. Science  1997,  276:  428 
• 4 Gross PE. Baker MA. Carver JP. Dennis JW. Clin. Cancer Res.  1995,  1:  935 
• 5a van den Broek LAMG. In Azasugars: Chemistry and their Biological Activity as Potential Anti-HIV Drugs, Carbohydrates in Drug Design   Witczak ZJ. Nieforth KA. Marcel Dekker; New York: 1997.  p.471 
• 5b Ratner L. Heyden NV. Dedera D. Virology  1991,  181:  180 
• Some representative recent articles:
• 6a Liu H. Liang X. Søhoel H. Bülow A. Bols M. J. Am. Chem. Soc.  2001,  123:  5116 
• 6b Ghavami A. Johnston BD. Jensen MT. Svensson B. Pinto BM. J. Am. Chem. Soc.  2001,  123:  6268 
• 6c Mao H. Joly GJ. Peeters K. Hoornaert GJ. Compernolle F. Tetrahedron  2001,  57:  6955 
• 6d Pandey G. Kapur M. Tetrahedron Lett.  2000,  41:  8821 
• 6e Enders D. Kirchhoff JH. Synthesis  2000,  2099 
• 6f Herdeis C. Telser J. Eur. J. Org. Chem.  1999,  1407 
• 6g Herdeis C. Schiffer T. Tetrahedron  1999,  55:  1043 
• 6h For a comprehensive recent review on stereoselective synthesis of Prosopis and Cassia piperidine alkaloids see: Laschat S. Dickner T. Synthesis  2000,  1781 
• 7 Tepfer D. Goldman A. Pamboukdjian N. Maille M. Lepingle A. Chevalier D. Denarie J. Rosenberg C. J. Bacteriol.  1988,  170:  1153 
• 8 Molyneux RJ. Nash RJ. Asano N. The Chemistry and Biological Activity of Calystegines and Related Nortropane Alkaloids, In Alkaloids: Chemical and Biological Perspectives   Vol. 11:  Pelletier SW. Pergamon; Oxford: 1996.  p.303 
• 9 Nash RJ. Asano N. Watson AA. Polyhydroxylated Alkaloids that Inhibit Glycosidases, In Alkaloids: Chemical and Biological Perspectives   Vol. 11:  Pelletier SW. Pergamon; Oxford: 1996.  p.346 
• 10a Kato A. Adachi I. Miyauchi M. Ikeda K. Komae T. Kizu H. Kameda Y. Watson AA. Nash RJ. Wormald MR. Fleet GWJ. Asano N. Carbohydr. Res.  1999,  316:  95 
• 10b Asano N. Kato A. Oseki K. Kizu H. Matsui K. Eur. J. Biochem.  1995,  229:  369 
• 11 Asano N. Kato A. Kizu H. Matsui K. Watson AA. Nash RJ. Carbohydr. Res.  1996,  293:  195 
• 12 Chapleur Y. Carbohydrate Mimics, Concepts and Methods   Wiley-VCH; Weinheim: 1998. 
• 13 García-Moreno MI. Benito JM. Mellet CO. García Fernández JM. J. Org. Chem.  2001,  66:  7604 
• 14 Koulocheri SD. Haroutounian SA. Synthesis  1999,  1889 
• 15 Ramsden NG. Fleet GWJ. Namgoong SK. J. Chem. Soc., Perkin Trans. 2  1991,  1991