Synthesis 2016; 48(21): 3753-3762
DOI: 10.1055/s-0035-1562438
paper
© Georg Thieme Verlag Stuttgart · New York

Synthesis of d-Fagomine and Its Seven- and Eight-Membered Higher-Ring Analogues, and the Formal Synthesis of (+)-Australine from l-Xylose-Derived Chiron

Pintu Das
Medicinal and Process Chemistry Division, CSIR-Central Drug Research Institute (CSIR-CDRI), Sector 10, Jankipuram Extension, Sitapur road, Lucknow-226031, U. P., India   eMail: akshaw55@yahoo.com
,
Sama Ajay
Medicinal and Process Chemistry Division, CSIR-Central Drug Research Institute (CSIR-CDRI), Sector 10, Jankipuram Extension, Sitapur road, Lucknow-226031, U. P., India   eMail: akshaw55@yahoo.com
,
Arun K. Shaw*
Medicinal and Process Chemistry Division, CSIR-Central Drug Research Institute (CSIR-CDRI), Sector 10, Jankipuram Extension, Sitapur road, Lucknow-226031, U. P., India   eMail: akshaw55@yahoo.com
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Publikationsverlauf

Received: 06. April 2016

Accepted after revision: 10. Mai 2016

Publikationsdatum:
29. Juni 2016 (online)


These authors contributed equally to this work.

Abstract

The synthesis of d-fagomine and its seven- and eight-membered higher-ring analogues from commercially available l-xylose is reported. The syntheses involve elaboration of a common alkenol precursor obtained from l-xylose-derived hemiacetal. The key steps in the syntheses are intramolecular reductive amination and ring-closing metathesis for the synthesis of d-fagomine and seven-/eight-membered iminosugar, respectively. We have also extended our synthetic strategy for the formal synthesis of (+)-australine using zinc-mediated fragmentation reaction and ring-closing metathesis as key steps.

Supporting Information

 
  • References

  • 1 Zechel DL, Withers SG. Acc. Chem. Res. 2000; 33: 11
  • 2 Cipolla L, La FB, Gregori M. Comb. Chem. High Throughput Screening 2006; 9: 571
    • 3a Elbein AD, Molyneux RJ In Iminosugars as Glycosidase Inhibitors . Stütz AE. Wiley-VCH; Weinheim: 1999. p 21
    • 3b Compain P, Martin OR In Iminosugars: From Synthesis to Therapeutic Applications . Wiley-VCH; Weinheim: 2007
    • 3c Mitrakou A, Tountas N, Raptis AE, Bauer RJ, Schulz H, Raptis SA. Diabetic Med. 1998; 15: 657
    • 3d Butters TD, Dwek RA, Platt FM. Curr. Top. Med. Chem. (Sharjah, United Arab Emirates) 2003; 3: 561
    • 3e Tyms AS, Berrie EM, Ryder TA, Nash RJ, Hegarty MP, Taylor DL, Mobberley MA, Davis JM, Bell EA, Jeffries DJ, Taylor-Robinson D, Fellows LE. Lancet 1987; 1025
    • 3f Datema R, Olafsson S, Romero PA. Pharmacol. Ther. 1987; 33: 221
    • 3g Karpas A, Fleet GW. J, Dwek RA, Petursson S, Namgoong SK, Ramsden NG, Jacob GS, Rademacher TW. Proc. Natl. Acad. Sci. U.S.A. 1988; 85: 9229
    • 3h Groopman EJ. Rev. Infect. Dis. 1990; 12: 931
    • 3i Karlsson GB, Butters TD, Dwek RA, Platt FM. J. Biol. Chem. 1993; 268: 570
    • 3j Wu S.-F, Lee C.-J, Liao C.-L, Dwek RA, Zitzmann N, Lin Y.-L. J. Virol. 2002; 8: 3596
    • 3k Saotome C, Wong CH, Kanie O. Chem. Biol. 2001; 8: 1061
    • 3l Goss PE, Baker MA, Carver JP, Dennis JW. Clin. Cancer Res. 1995; 1: 935
    • 3m Nishimura Y, Satoh T, Adachi H, Kondo S, Takeuchi T, Azetaka M, Fukuyasu H, Lizuka Y. J. Med. Chem. 1997; 40: 2626
    • 3n Asano N. Glycobiology 2003; 13: 93R
    • 3o Wrodnigg TM, Steiner AJ, Ueberbacher BJ. Anti-Cancer Agents Med. Chem. 2008; 8: 77
    • 3p Macchi B, Minutolo A, Grelli S, Cardona F, Cordero FM, Mastino A, Brandi A. Glycobiology 2010; 5: 500
    • 3q Holman RR, Cull CA, Turner RC. Diabetes Care 1999; 22: 960
    • 3r Scott LJ, Spencer CM. Drugs 2000; 59: 521
    • 3s Treadway JL, Mendy P, Hoover DJ. Drugs 2001; 10: 439
    • 3t Breuer HW. M. Int. J. Clin. Pharmacol. Ther. 2003; 41: 421
  • 4 Dragutan I, Dragutan V, Mitan C, Vosloo CM. H, Delaude L, Demonceau A. Beilstein J. Org. Chem. 2010; 6: 1188
    • 5a Goujon J.-Y, Gueyrard D, Compain P, Martin OR, Ikeda K, Kato A, Asano N. Bioorg. Med. Chem. 2005; 13: 2313
    • 5b Pearson MS. M, Math-Allainmat M, Fargeas V, Leberton J. Eur. J. Org. Chem. 2005; 2159
  • 6 Koyama M, Sakamura S. Agric. Biol. Chem. 1974; 38: 1111
  • 7 Molyneux RJ, Benson M, Wong RY, Tropea JE, Elbein AD. J. Nat. Prod. 1988; 51: 1198
  • 8 Asano N, Kato A, Miyauchi M, Kizu H, Tomimori T, Matsui K, Nash RJ, Molyneux RJ. Eur. J. Biochem. 1997; 248: 296
  • 9 Asano N, Kato A, Kizu H, Matsui K, Watson AA, Nash RJ. J. Nat. Prod. 1997; 60: 312
  • 10 Nojima H, Kimura I, Chen F.-J, Sugiura Y, Haruno M, Kato A, Asano N. J. Nat. Prod. 1998; 61: 397
  • 11 Fan J.-Q, Ishii S, Asano N, Suzuki Y. Nat. Med. 1999; 5: 112
    • 12a Kallam SR, Datrika R, Khobare SR, Gajare VS, Rajana N, Mohan HR, Babu JM, Siddaiah V, Pratap TV. Tetrahedron Lett. 2016; 57: 1351 ; and references cited therein
    • 12b Min IS, Kim SI, Hong S, Kim IS, Jung YH. Tetrahedron 2013; 69: 3901 ; and references cited therein
    • 12c Kundu PK, Ghosh SK. Tetrahedron: Asymmetry 2011; 22: 1090 ; and references cited therein
  • 13 Paulsen H, Todt K. Chem. Ber. 1967; 100: 512
    • 14a Qian X.-H, Moris VF, Wong C.-H. Bioorg. Med. Chem. Lett. 1996; 6: 1117
    • 14b Moris VF, Qian X.-H, Wong C.-H. J. Am. Chem. Soc. 1996; 118: 7647
    • 14c Qian X.-H, Moris F, Fitzgerald MC, Wong C.-H. Bioorg. Med. Chem. 1996; 4: 2055
    • 15a Godin G, Garnier E, Compain P, Martin OR, Ikeda K, Asano N. Tetrahedron Lett. 2004; 45: 579
    • 15b Jadhav VH, Bande OP, Puranik VG, Dhavale DD. Tetrahedron 2010; 66: 2830
  • 16 Chang MK, Kung YH, Ma CC, Chen ST. Tetrahedron 2007; 63: 1339
    • 17a Jadhav VH, Bande OP, Puranik VG, Dhavale DD. Tetrahedron 2010; 66: 2830
    • 17b Jagadeesh Y, Ramakrishna K, Rao BV. Tetrahedron: Asymmetry 2012; 23: 697
    • 17c Lee JC, Francis S, Dutta D, Gupta V, Yang Y, Zhu J.-Y, Tash JS, Schonbrunn E, Georg GI. J. Org. Chem. 2012; 77: 3082
    • 18a Lee JC, Francis S, Dutta D, Gupta V, Yang Y, Zhu J.-Y, Tash JS, Schonbrunn E, Georg GI. J. Org. Chem. 2012; 77: 3082
    • 18b Pearson WH, Hines JV. J. Org. Chem. 2000; 65: 5785
  • 19 Ramamurty CV. S, Ganney P, Rao CS, Fraser-Reid B. J. Org. Chem. 2011; 76: 2245
    • 21a Malone A, Scanlan EM. Org. Lett. 2013; 15: 504
    • 21b Tatibouet A, Rollin P, Martin OR. J. Carbohydr. Chem. 2000; 19: 641
  • 22 Seetharamsingh B, Rajamohanan PR, Reddy DS. Org. Lett. 2015; 17: 1652
  • 23 Kumari N, Reddy GB, Vankar YD. Eur. J. Org. Chem. 2009; 160
  • 24 Corkran HM, Munneke S, Dangerfield EM, Stocker BL, Timmer MS. M. J. Org. Chem. 2013; 78: 9791
    • 25a Zhu T, Yan Z, Chucholowsky A, Li R. J. Comb. Chem. 2005; 7: 520
    • 25b Theil F, Ballschuh S. Tetrahedron: Asymmetry 1996; 7: 3565
  • 26 Llaveria J, Díaz Y, Matheu MI, Castillón S. Eur. J. Org. Chem. 2011; 1514
  • 27 Li H, Blériot Y, Chantereau C, Mallet JM, Sollogoub M, Zhang Y, García ER, Vogel P, Barbero JJ, Sinaÿ P. Org. Biomol. Chem. 2004; 2: 1492
  • 28 Lauritsen A, Madsen R. Org. Biomol. Chem. 2006; 4: 2898
    • 29a Molyneux RJ, Benson M, Wong RY, Tropea JE, Elbein AD. J. Nat. Prod. 1988; 51: 1198
    • 29b Nash RJ, Fellows LE, Plant AC, Fleet GW. J, Derome AE, Baird PD, Hegarty MP, Scofield AM. Tetrahedron 1988; 44: 5959
    • 29c Fleet GW. J, Haraldsson M, Nash RJ, Fellows LE. Tetrahedron Lett. 1988; 29: 5441
    • 30a White JD, Hrnciar P. J. Org. Chem. 2000; 65: 9129
    • 30b White JD, Hrnciar P, Yokochi AF. T. J. Am. Chem. Soc. 1998; 120: 7359