Article Sidebar

Download
PDF

Main Article Content

Abstract

Stereoselective synthesis of terpene alcohol, β-citronellol is achieved in excellent yield by molecular iodine- and indium salts-catalyzed reactions with protected glycal and protected bromo sugar derivatives.

Keywords

Glycosylation Alcohol Terpene Catalysis

Article Details

How to Cite
Naresh Yadav, R., Sardar, S., & Krishna Banik, B. (2018). Highly Efficient Stereoselective Glycosylation of β-Citronellol. Asian Journal of Organic & Medicinal Chemistry, 3(3), 81–84. https://doi.org/10.14233/ajomc.2018.AJOMC-P109
Download Citation
Endnote/Zotero/Mendeley (RIS)
BibTeX

References

  1. B.K. Banik, M.S. Manhas and A.K. Bose, Enantiopure a-Hydroxy-b-Lactams via Stereoselective Glycosylation, Tetrahedron Lett., 38, 5077 (1997); https://doi.org/10.1016/S0040-4039(97)01130-1.
  2. B.K. Banik, O. Zegrocka, M.S. Manhas and A.K. Bose, Enantio-merically Pure b-Lactams with the Thienamycin Side Chain via Glycosy-lation, Heterocycles, 46, 173 (1997); https://doi.org/10.3987/COM-97-S66.
  3. B.K. Banik, M.S. Manhas and A.K. Bose, Stereospecific Glycosylation via Ferrier Rearrangement for Optical Resolution, J. Org. Chem., 59, 4714 (1994); https://doi.org/10.1021/jo00096a004.
  4. B.K. Banik, O. Zegrocka, M.S. Manhas and A.K. Bose, A Facile Iodine-Catalyzed Glycosylation: Enantiomerically Pure b-Lactams with the Thienamycin Side Chain, Heterocycles, 78, 2443 (2009); https://doi.org/10.3987/COM-09-11729.
  5. B.K. Banik and M.S. Manhas, Iodine-Catalyzed Stereospecific Glycosy-lation of Alcohols: Enantiopure b-Lactams, Tetrahedron Symposium-in-Print, 68, 10769 (2012).
  6. B.K. Banik, C. Mukhopadhya and C. Logan, Optical Resolution of Dibenzo[a,g]fluorenol via Glycosylation, Synth. Commun., 37, 3895 (2007); https://doi.org/10.1080/00397910701572209.
  7. B.K. Banik, I. Banik and F.F. Becker, Asymmetric Synthesis of Anti-cancer b-Lactams via Staudinger Reaction: Utilization of Chiral Ketene from Carbohydrate, Eur. J. Med. Chem., 45, 846 (2010); https://doi.org/10.1016/j.ejmech.2009.11.024.
  8. B.K. Banik, S. Samajdar, I. Banik, O. Zegrocka and F.F. Becker, Indium-mediated Stereospecific Glycosylation of Alcohols, Heterocycles, 55, 227 (2001); https://doi.org/10.3987/COM-00-9100.
  9. I. Banik, S. Samajdar and B.K. Banik, Stereospecific Chiral Resolution of trans-2-Phenylcyclohexanol via Indium-Induced Glycosylation, Heterocycl. Lett., 1, 47 (2011).
  10. S. Samajdar, I. Banik and B.K. Banik, Indium-Induced Highly Stereo-selective Thioglycosylation of Peracetylated Bromoglucose, Heterocycl. Lett., 1, 41 (2011).
  11. B.K. Banik, S. Samajdar and F.F. Becker, Asymmetric Synthesis of Anticancer b-Lactams via Staudinger Reaction, Mol. Med. Rep., 3, 319 (2010).
  12. S. Chandra, R.N. Yadav, A. Paniagua and B.K. Banik, Indium Salts-Catalyzed O and S-Glycosylation of Bromo Sugar with Benzyl Glycolate: An Unprecedented Hydrogenolysis, Tetrahedron Lett., 57, 1425 (2016); https://doi.org/10.1016/j.tetlet.2016.02.039.
  13. B.K. Banik, I. Garcia, F.R. Morales and C. Aguilar, Novel Synthesis of Substituted Pyrrole Bound to Indolinone via Molecular Iodine-Catalyzed Reaction, Heterocycl. Commun., 13, 109 (2007); https://doi.org/10.1515/HC.2007.13.2-3.109.
  14. B.K. Banik and M. Cardona, Bismuth Nitrate-Catalyzed Novel Synthesis of Pyrrole-Substituted Indolinones, Tetrahedron Lett., 47, 7385 (2006); https://doi.org/10.1016/j.tetlet.2006.07.150.
  15. S. Samajdar, M.K. Basu, F.F. Becker and B.K. Banik, A New Molecular Iodine-Catalyzed Thioketalization of Carbonyl Compounds: Selectivity and Scope, Tetrahedron Lett., 42, 4425 (2001); https://doi.org/10.1016/S0040-4039(01)00752-3.
  16. M.K. Basu, S. Samajdar, F.F. Becker and B.K. Banik, A New Molecular Iodine-Catalyzed Acetalization of Carbonyl Compounds, Synlett, 319 (2002); https://doi.org/10.1055/s-2002-19774.
  17. B.K. Banik, M. Chapa, J. Marquez and M. Cardona, A Remarkable Iodine-Catalyzed Protection of Carbonyl Compounds, Tetrahedron Lett., 46, 2341 (2005); https://doi.org/10.1016/j.tetlet.2005.01.176.
  18. B.K. Banik and R. Garza, Iodine-Catalyzed Facile Deprotection of Acetal and Ketal in Acetone, Chem. Educ., 12, 75 (2007).
  19. D. Bandyopadhyay, J. Cruz, R.N. Yadav and B.K. Banik, An Expedi-tious Iodine-Catalyzed Synthesis of 3-Pyrrole-substituted 2-Azetidi-nones, Molecules, 17, 11570 (2012); https://doi.org/10.3390/molecules171011570.
  20. B.K. Banik, S. Samajdar and I. Banik, Simple Synthesis of Substituted Pyrroles, J. Org. Chem., 69, 213 (2004); https://doi.org/10.1021/jo035200i.
  21. D. Bandyopadhyay, G. Rivera, I. Salinas, H. Aguilar and B.K. Banik, Remarkable Iodine-Catalyzed Synthesis of Novel Pyrrole- Bearing N-Polyaromatic b-Lactams, Molecules, 15, 1082 (2010); https://doi.org/10.3390/molecules15021082.
  22. D. Bandyopadhyay, S. Mukherjee and B.K. Banik, An Expeditious Synthesis of N-substituted Pyrroles via Microwave-Induced Iodine-Catalyzed Reactions under Solventless Conditions, Molecules, 15, 2520 (2010); https://doi.org/10.3390/molecules15042520.
  23. B.K. Banik, M. Fernandez and C. Alvarez, Iodine-Catalyzed Highly Efficient Michael Reaction of Indoles under Solvent-Free Condition, Tetrahedron Lett., 46, 2479 (2005); https://doi.org/10.1016/j.tetlet.2005.02.044.
  24. P. Parvatkar, P.S. Prameswaran, D. Bandyopadhyay, S. Mukherjee and B.K. Banik, Iodine-Catalyzed Novel Synthesis of Carbazoles, Curr. Microw. Chem., 4, 238 (2017); https://doi.org/10.2174/2213335604666170412162854.
  25. D. Bandyopadhyay, S. Mukherjee, R.R. Rodriguez and B.K. Banik, An Effective Microwave-Induced Iodine-Catalyzed Method for the Synthesis of Quinoxalines via Condensation of 1,2-Diamines with 1,2-Dicarbonyl Compounds, Molecules, 15, 4207 (2010); https://doi.org/10.3390/molecules15064207.
  26. B.K. Banik, A. Ghatak and F.F. Becker, Indium-Mediated Facile Synthesis of 3-Unsubstituted b-Lactams, J. Chem. Soc., Perkin Trans. 1, 2179 (2000); https://doi.org/10.1039/b002833i.
  27. A. Ghatak, F.F. Becker and B.K. Banik, Indium-Mediated Facile Synthesis of 3-Unsubstituted Ferrocenyl b-Lactams, Heterocycles, 53, 2769 (2000); https://doi.org/10.3987/COM-00-9019.
  28. S. Chandra, R.N. Yadav, L. Lareeb and B.K. Banik, Synthesis of 3-Unsub-stituted b-Lactams using Radical Reactions, Chem. Educ., 20, 4 (2015).
  29. A. Ghatak and B.K. Banik, Indium-Induced Reformatsky Reaction for the Synthesis of b-Lactams, Heterocycl. Lett., 1, 99 (2011).
  30. B.K. Banik, M. Suhendra, I. Banik and F.F. Becker, Indium/Ammonium Chloride Mediated Selective Reduction of Aromatic Nitro Compounds: Practical Synthesis of 6-Amino Chrysene, Synth. Commun., 30, 3745 (2000); https://doi.org/10.1080/00397910008087002.
  31. B.K. Banik, I. Banik, S. Samajdar and M. Wilson, Facile Synthesis of Biologically Active Heterocycles by Indium-Induced Reactions of Aromaic Nitro Compounds in Aqueous Ethanol, Heterocycles, 63, 283 (2004); https://doi.org/10.3987/COM-03-9914.
  32. B.K. Banik, I. Banik and F.F. Becker, Indium/Ammonium Chloride-Mediated Selective Reduction of Aromatic Nitro Compounds: Ethyl 4-Aminobenzoate, Org. Synth., 81, 188 (2004); https://doi.org/10.15227/orgsyn.081.0188.
  33. B.K. Banik, I. Banik, L. Hackfeld and F.F. Becker, Indium-Mediated Reductive Cyclizations in Aqueous Ethanol: Highly Efficient Synthesis of Heterocyclic Compounds of Biological Interests, Heterocycles, 56, 467 (2001); https://doi.org/10.3987/COM-00-S(K)3.
  34. B.K. Banik, S. Samajdar and I. Banik, A Facile Synthesis of Oxazines by Indium-Induced Reduction-Rearrangement of the Nitro b-Lactams, Tetrahedron Lett., 44, 1699 (2003); https://doi.org/10.1016/S0040-4039(02)02823-X.
  35. B.K. Banik, L. Hackfeld and F.F. Becker, Studies on the Indium-Mediated Reduction of Imines, Synth. Commun., 31, 1581 (2001); https://doi.org/10.1081/SCC-100104072.
  36. D. Abrego, D. Banyopadhyay and B.K. Banik, Indium-Induced Synthesis of Pyrrole-Substituted Indole Derivatives, Heterocycl Lett., 1, 87 (2011).
  37. B.K. Banik, Heterocyclic Scaffolds I, In: Topics in Heterocyclic Chemistry, Springer, vol. 22, p. 1 (2010).
  38. B.K. Banik, b-Lactams: Synthesis and Biological Evaluation, In: Topics in Heterocyclic Chemistry, Springer, vol. 30, pp. 1-226 (2012).
  39. I. Banik and B.K. Banik, Microwave-Induced Chemical Manipulation of b-Lactam, Springer, vol. 88, pp. 781-1007 (2012).
  40. B.K. Banik, Beta Lactams: Novel Synthetic Pathways and Applications, Springer, pp. 1-419 (2017).
  41. P.T. Parvatkar, P.S. Parameswaran and B.K. Banik, ed.: B.K. Banik, Solid Phase Synthesis of b-Lactams: Results and Scope, In: Beta Lactams: Novel Synthetic Pathways and Applications, Springer, pp. 253-284 (2017).
  42. S. Basu and B.K. Banik, ed.: B.K. Banik, Beta Lactams as Clinically Active Molecules, In: Beta Lactams: Novel Synthetic Pathways and Applications, Springer, pp. 285-310 (2017).
  43. B.K. Banik, Synthesis and Biological Studies of Novel b-Lactams, CRC Book, pp. 31-72 (2013).