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Synlett 2013; 24(18): 2427-2430
DOI: 10.1055/s-0033-1339905
DOI: 10.1055/s-0033-1339905
letter
Direct Access to Iminosugars through an Interrupted Kondrat’eva Reaction
Further Information
Publication History
Received: 02 August 2013
Accepted after revision: 12 September 2013
Publication Date:
07 October 2013 (online)
Abstract
A concise synthesis of an iminosugar from an oxazole is presented that involves an interrupted inverse electron-demand Kondrat’eva reaction.
Supporting Information
- for this article is available online at http://www.thieme-connect.com/ejournals/toc/synlett.
- Supporting Information
-
References and Notes
- 1 Inoue S, Tsuruoka T, Niida T. J. Antibiot. 1966; 19: 288
- 2a Iminosugars: From Synthesis to Therapeutic Applications . Compain P, Martin OR. John Wiley and Sons; West Sussex: 2007
- 2b Asano N In Glycoscience . Fraser-Reid BO, Tatsuta K, Thiem J. Springer; Berlin: 2008: 1887
- 3 Asano N, Tomioka E, Kizu H, Matsui K. Carbohydr. Res. 1994; 253: 235
- 4 Koyama M, Sakamura S. Agric. Biol. Chem. 1974; 38: 1111
- 5 Hohenschutz LD, Bell EA, Jewess PJ, Leworthy DP, Pryce RJ, Arnold E, Cladry J. Phytochemistry 1981; 20: 811
- 6 Asano N, Kuroi H, Ikeda K, Kizu H, Kameda Y, Kato A, Adachi I, Watson AA, Nash RJ, Fleet GW. J. Tetrahedron: Asymmetry 2000; 11: 1
- 7a D’Alonzo D, Guaragna A, Palumbo G. Curr. Med. Chem. 2009; 16: 473
- 7b Iminosugars as Glycosidase Inhibitors: Nojirimycin and Beyond. Stütz AE. Wiley-VCH; New York: 1999
- 7c Asano N. Glycobiology 2003; 13: 93R
- 8a Cox T, Lachmann R, Hollak C, Aerts J, van Weely S, Hrebícek M, Platt F, Butters T, Dwek R, Moyses C, Gow I, Elstein D, Zimran A. Lancet 2000; 355: 1481
- 8b Platt FM, Neises GR, Dwek RA, Butters TD. J. Biol. Chem. 1994; 269: 8362
- 8c Platt FM, Neises GR, Karlsson GB, Dwek RA, Butters TD. J. Biol. Chem. 1994; 269: 27108
- 9 Scott LJ, Spencer CM. Drugs 2000; 59: 521
- 10a Dhand V, Draper JA, Moore J, Britton R. Org. Lett. 2013; 15: 1914
- 10b Toumieux S, Compain P, Martin OR. J. Org. Chem. 2008; 73: 2155
- 10c Guo H, O’Doherty GA. Org. Lett. 2006; 8: 1609
- 10d Liao W.-W, Ibrahem I, Córdova A. Chem. Commun. 2006; 674
- 10e Calderón F, Doyagüez EG, Fernández-Mayoralas A. J. Org. Chem. 2006; 71: 6258
- 11 Wenkert D, Chen T.-F, Ramachandran K, Valasinas L, Weng L.-l, McPhail AT. Org. Lett. 2001; 3: 2301
- 12a Hassner A, Fischer B. Heterocycles 1993; 35: 1441
- 12b Lipshutz BH. Chem. Rev. 1986; 86: 795
- 12c Boger DL. Tetrahedron 1983; 39: 2869
- 12d Turchi IJ, Dewar MJ. S. Chem. Rev. 1975; 75: 389
- 12e Karpeiskii MY, Florent’ev VL. Russ. Chem. Rev. 1969; 38: 540
- 12f Kondrat’eva GY. Khim. Nauka Prom. 1957; 2: 666
- 12g Kondrat’eva GY. Izu. Akad. Nauk. SSSR, Sre. Khim. 1959; 484
-
13a Lehmann J, Alzieu T, Martin RE, Britton R. Org. Lett. 2013; 15: 3550
- 13b Basch CH, Brinck JA, Ramos JE, Habay SA, Yap GP. A. J. Org. Chem. 2012; 77: 10416
-
13c Suarez-Moreno GV, Gonzalez-Zamora E, Mendez F. Org. Lett. 2011; 13: 6358
- 14a Fallis AG. Can. J. Chem. 1984; 62: 183
- 14b Craig D. Chem. Soc. Rev. 1987; 16: 187
- 14c Fallis AG. Acc. Chem. Res. 1999; 32: 464
- 14d Takao K.-i, Munakata R, Tadano K.-i. Chem. Rev. 2005; 105: 4779
- 14e Juhl M, Tanner D. Chem. Soc. Rev. 2009; 38: 2983
- 15a Ainsworth PJ, Craig D, Reader JC, Slawin AM. Z, White AJ. P, Williams DJ. Tetrahedron 1996; 52: 695
- 15b Craig D, Ford MJ, Stones JA. Tetrahedron Lett. 1996; 37: 535
- 15c Craig D, Reader JC. Tetrahedron Lett. 1990; 31: 6585
- 15d Kraus GA, Bougie D. J. Org. Chem. 1989; 54: 2425
- 15e Funk RL, Mossman CJ, Zeller WE. Tetrahedron Lett. 1984; 25: 1655
- 15f White JD, Sheldon BG. J. Org. Chem. 1981; 46: 2273
- 15g Fráter G. Tetrahedron Lett. 1976; 17: 4517
- 16a Denmark SE, Cottel JJ. J. Org. Chem. 2001; 66: 4276
- 16b Denmark SE, Martinborough EA. J. Am. Chem. Soc. 1999; 121: 3046
- 16c Arribas C, Carreño MC, García-Ruano JL, Rodríguez JF, Santos M, Sanz-Tejedor MA. Org. Lett. 2000; 2: 3165
- 17 Gillard JW, Fortin R, Grimm EL, Maillard M, Tjepkema M, Bernstein MA, Glaser R. Tetrahedron Lett. 1991; 32: 1145
- 18a Meerwein’s Salt In Name Reactions: A Collection of Detailed Mechanisms and Synthetic Applications. Li JJ. Springer; Berlin: 2009: 343
- 18b Meerwein H, Hinz G, Hofmann P, Pfeil E. J. Prakt. Chem. 1937; 147: 257
- 19 It is noteworthy that there was no indication of pyridinium formation through a cycloaddition dehydration process in any of these experiments.
- 20a Posner GH, Cho C.-G, Anjeh TE. N, Johnson N, Horst RL, Kobayashi T, Okano T, Tsugawa N. J. Org. Chem. 1995; 60: 4617
- 20b Ojima I, Kogure T. Organometallics 1982; 1: 1390
- 21 See Supporting Information for copies of NMR spectra (1H, 13C, HSQC, HMBC) recorded on the iminosugar 26.
For examples of de novo iminosugar synthesis, see:
For reviews on intramolecular Diels–Alder reactions, see:
For the use of removable tethers in intramolecular Diels–Alder reactions, see:
For examples of Diels–Alder reactions in iminosugar synthesis, see: