Synthesis 2016; 48(08): 1191-1196
DOI: 10.1055/s-0035-1561365
paper
© Georg Thieme Verlag Stuttgart · New York

Stereoselective Total Synthesis of Unnatural (+)-Anisomycin

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
,
Puli Saidhareddy
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
› Author Affiliations
Further Information

Publication History

Received: 14 December 2015

Accepted after revision: 18 January 2016

Publication Date:
10 February 2016 (online)


Abstract

Stereoselective total synthesis of unnatural (+)-anisomycin from d-glucose has been achieved with an overall yield of 23%. The key synthetic features are regioselective opening of an epoxide, azidation of the resulting alcohol, and finally one-pot hydrogenation leading to cyclization to the pyrrolidine ring in a single step.

Supporting Information

 
  • References

  • 1 Sobin BA, Tanner FW. J. Am. Chem. Soc. 1954; 76: 4053
    • 2a Ishida S, Yamada O, Futatsuya F, Ito K, Yamamoto H, Munakata K. Proceedings of the First Intersectional Congress of IAMS . Vol. 3. Hasegawa T. Science Council of Japan; Tokyo: 1975: 641
    • 2b Hosoya Y, Kameyama T, Naganawa H, Okami Y, Takeuchi T. J. Antibiot. 1993; 46: 1300
  • 3 Beereboom JJ, Butler K, Pennington FC, Solomons IA. J. Org. Chem. 1965; 30: 2334
  • 4 Wong CM. Can. J. Chem. 1968; 46: 1101
  • 5 Schaefer JP, Wheatley PJ. J. Org. Chem. 1968; 33: 166
    • 6a Jimenez A, Vazquez D In Antibiotics . Hahn FE. Springer; Berlin: 1979: 1-19
    • 6b Grollman AP. J. Biol. Chem. 1967; 242: 3226
  • 7 Schwartdt O, Veith U, Gaspard C, Jager V. Synthesis 1999; 1473
  • 8 Santander VM, Cue AB, Diaz JG. H, Balmis FJ, Miranda G, Urbina E, Portilla J, Plata AA, Zapata HB, Munoz VA, Abreu LM. Rev. Invest. Biol. Univ. Guadalajara 1961; 1: 94
    • 9a Frye WW, Mule JG, Swartzwelder C. Antibiot. Annu. 1955; 820
    • 9b Armstrong T, Santa Maria O. Antibiot. Annu. 1955; 824
  • 10 Korzybski T, Kowszyk-Gindifer Z, Kurytowicz W. Antibiotics . Vol. 1. American Society of Microbiology; Washington DC: 1978: 343-346
    • 11a Kim JH, Curtis-Long MJ, Woo DS, Jin HL, Byong WL, Yong JY, Kyu YK, Park KH. Bioorg. Med. Chem. Lett. 2005; 15: 4282
    • 11b Chapman TM, Courtney S, Hay P, Davis BG. Chem.Eur. J. 2003; 9: 3397

      For recent literature:
    • 12a Zeng J, Zhang Q, Zhang HK, Chen A. RSC Adv. 2013; 3: 20298
    • 12b Li J, Feng YH, Li XB, Han W, Liu HQ, Shao GG. Chin. Chem. Lett. 2012; 23: 647
    • 12c Chouthaiwale PV, Kotkar SP, Sudalai A. ARKIVOC 2009; (ii): 88
    • 12d Joo J.-E, Lee K.-Y, Pham V.-T, Tian Y-S, Ham W.-H. Org. Lett. 2007; 9: 3627
    • 12e Kim JH, Curtis-Long MJ, Seo WD, Ryu YB, Yang MS, Park KH. J. Org. Chem. 2005; 70: 4082; and references cited therein
    • 12f Hulme AN, Rosser EM. Org. Lett. 2002; 4: 265 ; and references cited therein
    • 13a Detz RJ, Abiri Z, Griel RL, Hiemstra H, Maarseveen JH. V. Chem. Eur. J. 2011; 17: 5921
    • 13b Reddy KS, Rao BV. Tetrahedron: Asymmetry 2011; 22: 190
    • 13c Reddy JS, Kumar AR, Rao BV. Tetrahedron: Asymmetry 2005; 16: 3154
    • 13d Meyers AI, Dupre B. Heterocycles 1987; 113
    • 13e Wong CM, Buccini J, Chang I, Te Raa J, Schwenk R. Can. J. Chem. 1969; 47: 2421
    • 13f Wong CM, Buccini J, Te Raa J. Can. J. Chem. 1968; 46: 3091
    • 14a Arora I, Kashyap VK, Singh AK, Dasgupta A, Kumar B, Shaw AK. Org. Biomol. Chem. 2014; 12: 6855
    • 14b Das P, Kundooru S, Pandole R, Sharma SK, Singh BN, Shaw AK. Tetrahedron: Asymmetry 2016; 27: 101
  • 15 Morillo M, Lequart V, Grand E, Goethals G, Usubillaga A, Villa P, Martin P. Carbohydr. Res. 2001; 334: 281
  • 16 Meurillon M, Marton Z, Hospital A, Jordheim LP, Béjaud J, Lionne C, Dumontet C, Périgaud C, Chaloin L, Peyrottes S. Eur. J. Med. Chem. 2014; 77: 18
  • 17 Mereyala HB, Gadikota RR. Tetrahedron: Asymmetry 1998; 9: 827
  • 18 Kundooru S, Das P, Meena S, Kumar V, Siddiqi MI, Datta D, Shaw AK. Org. Biomol. Chem. 2015; 13: 8241
    • 19a Kaden S, Brockmann M, Reissig H.-U. Helv. Chim. Acta 2005; 88: 1826
    • 19b Kang SH, Choi H.-W. Chem. Commun. 1996; 1521
    • 20a Horne G, Wilson FX, Tinsley J, Williams DH, Storer R. Drug Discovery Today 2011; 16: 107
    • 20b Horne G, Wilson FX. Prog. Med. Chem. 2011; 50: 135
    • 20c Nash RJ, Kato A, Yu CY, Fleet GW. J. Future Med. Chem. 2011; 3: 1513
    • 20d Compain P, Martin OR. Iminosugars: From Synthesis to Therapeutics Applications . John Wiley; Chichester: 2007