Table of Contents
ISRN Organic Chemistry
Volume 2014, Article ID 767954, 5 pages
http://dx.doi.org/10.1155/2014/767954
Research Article

A Facile Stereoselective Total Synthesis of (R)-Rugulactone

1Polymer Science and Engineering Division, National Chemical Laboratory, Pashan, Pune 411 008, India
2Bharati Vidyapeeth University, Advanced Research Centre in Pharmaceutical Sciences & Applied Chemistry, Poona College of Pharmacy, Erandwane, Pune 411038, India

Received 15 December 2013; Accepted 6 January 2014; Published 30 March 2014

Academic Editors: A. Barbero and F. L. Van Delft

Copyright © 2014 B. Narasimha Reddy and R. P. Singh. This is an open access article distributed under the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

Linked References

  1. S. E. Drewes, B. M. Sehlapelo, M. M. Horn, R. Scott-Shaw, and P. Sandor, “5,6-Dihydro-α-pyrones and two bicyclic tetrahydro-α-pyrone derivatives from Cryptocarya latifolia,” Phytochemistry, vol. 38, no. 6, pp. 1427–1430, 1995. View at Google Scholar · View at Scopus
  2. S. E. Drewes, M. M. Horn, and R. S. Shaw, “alpha-Pyrones and their derivatives from two Cryptocarya species,” Phytochemistry, vol. 40, no. 1, pp. 321–323, 1995. View at Publisher · View at Google Scholar · View at Scopus
  3. S. D. Rychnovsky, “Oxo polyene macrolide antibiotics,” Chemical Reviews, vol. 95, no. 6, pp. 2021–2040, 1995. View at Google Scholar · View at Scopus
  4. M. Carda, S. Rodrguez, F. Gonzalez, E. Castillo, A. Villanueva, and J. A. Marco, “Stereoselective synthesis of the naturally occurring lactones (-)-osmundalactone and (-)-muricatacine using ring-closing metathesis,” European Journal of Organic Chemistry, pp. 2649–2655, 2002. View at Google Scholar
  5. H. Kikuchi, K. Sasaki, J. Sekiya et al., “Structural requirements of dictyopyrones isolated from Dictyostelium spp. in the regulation of Dictyostelium development and in anti-leukemic activity,” Bioorganic and Medicinal Chemistry, vol. 12, no. 12, pp. 3203–3214, 2004. View at Publisher · View at Google Scholar · View at Scopus
  6. R. Pereda-Mirinda, M. Fragoso-Serranoa, and C. M. Cerda-García-Rojasb, “Application of molecular mechanics in the total stereochemical elucidation of spicigerolide, a cytotoxic 6-tetraacetyloxyheptenyl-5,6-dihydro-α-pyrone from Hyptis spicigera,” Tetrahdron, vol. 57, pp. 47–53, 2001. View at Publisher · View at Google Scholar
  7. A. Fatima, L. K. Kohn, M. A. Antonio, J. E. de Carvalho, and R. A. Pillia, “(R)-Goniothalamin: total syntheses and cytotoxic activity against cancer cell lines,” Bioorganic & Medicinal Chemistry, vol. 13, pp. 2927–2933, 2005. View at Publisher · View at Google Scholar
  8. G. F. Spencer, R. E. England, and R. B. Wolf, “(-)-Cryptocaryalactone and (-)-deacetylcryptocaryalactone-germination inhibitors from Cryptocarya moschata seeds,” Phytochemistry, vol. 23, no. 11, pp. 2499–2500, 1984. View at Google Scholar · View at Scopus
  9. T. R. Govindachari, P. C. Parthasarathy, H. K. Desai, and M. N. Shanbhag, “Structure of cryptocaryone. A constituent of Cryptocarya bourdilloni gamb,” Tetrahedron, vol. 29, no. 19, pp. 3091–3094, 1973. View at Google Scholar · View at Scopus
  10. J. Jodynis-Liebert, M. Murias, and E. Błoszyk, “Effect of sesquiterpene lactones on antioxidant enzymes and some drug- metabolizing enzymes in rat liver and kidney,” Planta Medica, vol. 66, no. 3, pp. 199–205, 2000. View at Publisher · View at Google Scholar · View at Scopus
  11. S. Zschocke and J. Van Staden, “Cryptocarya species—substitute plants for Ocotea bullata? A pharmacological investigation in terms of cyclooxygenase-1 and -2 inhibition,” Journal of Ethnopharmacology, vol. 71, no. 3, pp. 473–478, 2000. View at Publisher · View at Google Scholar · View at Scopus
  12. S. E. Drewes, M. H. Horn, and S. Mavi, “Cryptocarya liebertiana and Ocotea bullata—their phytochemical relationship,” Phytochemistry, vol. 44, no. 3, pp. 437–440, 1997. View at Publisher · View at Google Scholar · View at Scopus
  13. T. L. Meragelman, D. A. Scudiero, R. E. Davis et al., “Inhibitors of the NF-κB activation pathway from cryptocarya rugulosa,” Journal of Natural Products, vol. 72, no. 3, pp. 336–339, 2009. View at Publisher · View at Google Scholar · View at Scopus
  14. M. Karin, “Nuclear factor-κB in cancer development and progression,” Nature, vol. 441, no. 7092, pp. 431–436, 2006. View at Publisher · View at Google Scholar · View at Scopus
  15. L. M. Coussens and Z. Werb, “Inflammation and cancer,” Nature, vol. 420, no. 6917, pp. 860–867, 2002. View at Publisher · View at Google Scholar · View at Scopus
  16. G. Sethi, B. Sung, and B. B. Aggarwal, “Nuclear factor-κB activation: from bench to bedside,” Experimental Biology and Medicine, vol. 233, pp. 21–31, 2008. View at Publisher · View at Google Scholar
  17. J.-L. Luo, H. Kamata, and M. Karin, “IKK/NF-κB signaling: balancing life and death—a new approach to cancer therapy,” Journal of Clinical Investigation, vol. 115, no. 10, pp. 2625–2632, 2005. View at Publisher · View at Google Scholar · View at Scopus
  18. F. R. Greten and M. Karin, “The IKK/NF-κB activation pathway—a target for prevention and treatment of cancer,” Cancer Letters, vol. 206, no. 2, pp. 193–199, 2004. View at Publisher · View at Google Scholar · View at Scopus
  19. D. K. Mohapatra, P. P. Das, D. Sai Reddy, and J. S. Yadav, “First total syntheses and absolute configuration of rugulactone and 6(R)-(4′-oxopent-2′-enyl)-5,6-dihydro-2H-pyran-2-one,” Tetrahedron Letters, vol. 50, no. 43, pp. 5941–5944, 2009. View at Publisher · View at Google Scholar · View at Scopus
  20. F. Allais, M. Aouhansou, A. Majira, and P.-H. Ducrot, “Asymmetric total synthesis of rugulactone, an α-pyrone from Cryptocarya rugulosa,” Synthesis, no. 16, pp. 2787–2793, 2010. View at Publisher · View at Google Scholar · View at Scopus
  21. D. K. Reddy, V. Shekhar, T. S. Reddy, S. P. Reddy, and Y. Venkateswarlu, “Stereoselective first total synthesis of (R)-rugulactone,” Tetrahedron Asymmetry, vol. 20, no. 20, pp. 2315–2319, 2009. View at Publisher · View at Google Scholar · View at Scopus
  22. D. K. Reddy, V. Shekhar, P. Prabhakar et al., “Stereoselective synthesis and biological evaluation of (R)-rugulactone, (6R)-((4R)-hydroxy-6-phenyl-hex-2-enyl)-5,6-dihydro-pyran-2-one and its 4S epimer,” European Journal of Medicinal Chemistry, vol. 45, no. 10, pp. 4657–4663, 2010. View at Publisher · View at Google Scholar · View at Scopus
  23. G. Reddipalli, M. Venkataiah, and N. W. Fadnavis, “Chemo-enzymatic synthesis of both enantiomers of rugulactone,” Tetrahedron Asymmetry, vol. 21, no. 3, pp. 320–324, 2010. View at Publisher · View at Google Scholar · View at Scopus
  24. F. Cros, B. Pelotier, and O. Piva, “Regioselective tandem ring closing/cross metathesis of 1,5-hexadien-3-ol derivatives: application to the total synthesis of rugulactone,” European Journal of Organic Chemistry, no. 26, pp. 5063–5070, 2010. View at Publisher · View at Google Scholar · View at Scopus
  25. B. Dietrich, E. Fernandez, and P. Jorg, “Stereoselective synthesis of both enantiomers of rugulactone,” The Journal of Organic Chemistry, vol. 76, no. 9, pp. 3463–3469, 2011. View at Google Scholar
  26. G. Sabitha, V. Bhaskar, and J. S. Yadav, “The first asymmetric total synthesis of (R)-tuberolactone, (S)-jasmine lactone and (R)-δ-decalactone,” Tetrahedron Letters, vol. 47, no. 46, pp. 8179–8181, 2006. View at Publisher · View at Google Scholar · View at Scopus
  27. G. C. G. Pais, R. A. Fernandes, and P. Kumar, “Asymmetric synthesis of (S)-Massoialactone,” Tetrahedron, vol. 55, no. 47, pp. 13445–13450, 1999. View at Publisher · View at Google Scholar · View at Scopus
  28. S. E. Bode, M. Wolberg, and M. Müller, “Stereoselective synthesis of 1,3-diols,” Synthesis, no. 4, pp. 557–588, 2006. View at Publisher · View at Google Scholar
  29. J. S. Yadav and C. S. Reddy, “Stereoselective synthesis of amphidinolide T1,” Organic Letters, vol. 11, no. 8, pp. 1705–1708, 2009. View at Publisher · View at Google Scholar · View at Scopus
  30. T. Katsuki and K. B. Sharpless, “The first practical method for asymmetric epoxidation,” Journal of the American Chemical Society, vol. 102, no. 18, pp. 5974–5976, 1980. View at Google Scholar · View at Scopus
  31. Y. Gao, R. M. Hanson, J. M. Klunder, S. Y. Ko, H. Masamune, and K. B. Sharpless, “Catalytic asymmetric epoxidation and kinetic resolution: modified procedures including in situ derivatization,” Journal of the American Chemical Society, vol. 109, no. 19, pp. 5765–5780, 1987. View at Google Scholar · View at Scopus
  32. T. Katsuki, P. M. Lee, V. S. Martin et al., “Synthesis of saccharides and related polyhydroxylated natural products. 1. Simple alditols,” The Journal of Organic Chemistry, vol. 47, pp. 1376–1380, 1982. View at Publisher · View at Google Scholar
  33. J. M. Finan and Y. Kishi, “Reductive ring openings of allyl-alcohol epoxides,” Tetrahedron Letters, vol. 23, no. 27, pp. 2719–2722, 1982. View at Google Scholar · View at Scopus
  34. K. D. Philips, J. Žemlička, and J. P. Horwitz, “Unsaturated sugars I. Decarboxylative elimination of methyl 2,3-di-O-benzyl-α-D-glucopyranosiduronic acid to methyl 2,3-di-O-benzyl-4-deoxy-β-L-threo-Pent-4-enopyranoside,” Carbohydrate Research, vol. 30, pp. 281–283, 1973. View at Publisher · View at Google Scholar
  35. W. C. Still and C. Gennari, “Direct synthesis of Z-unsaturated esters. A useful modification of the horner-emmons olefination,” Tetrahedron Letters, vol. 24, no. 41, pp. 4405–4408, 1983. View at Google Scholar · View at Scopus
  36. J. S. Yadav, B. V. Subba Reddy, and P. Vishnumurthy, “The cation exchange resin-promoted coupling of alkynes with aldehydes: one-pot synthesis of α,β-unsaturated ketones,” Tetrahedron Letters, vol. 49, no. 29-30, pp. 4498–4500, 2008. View at Publisher · View at Google Scholar · View at Scopus
  37. R. H. Grubbs, “Olefin metathesis,” Tetrahedron, vol. 60, no. 34, pp. 7117–7140, 2004. View at Publisher · View at Google Scholar · View at Scopus
  38. R. R. Schrock and A. H. Hoveyda, “Molybdenum and tungsten imido alkylidene complexes as efficient olefin-metathesis catalysts,” Angewandte Chemie—International Edition, vol. 42, no. 38, pp. 4592–4633, 2003. View at Publisher · View at Google Scholar · View at Scopus
  39. A. Furstner, “Olefin metathesis and beyond,” Angewandte Chemie—International Edition, vol. 39, no. 17, pp. 3012–3043, 2002. View at Google Scholar
  40. A. K. Chatterjee, T.-L. Choi, D. P. Sanders, and R. H. Grubbs, “A general model for selectivity in olefin cross metathesis,” Journal of the American Chemical Society, vol. 125, no. 37, pp. 11360–11370, 2003. View at Publisher · View at Google Scholar · View at Scopus
  41. G. Reddipalli, M. Venkataiah, and N. W. Fadnavis, “Chemo-enzymatic synthesis of both enantiomers of rugulactone,” Tetrahedron Asymmetry, vol. 21, no. 3, pp. 320–324, 2010. View at Publisher · View at Google Scholar · View at Scopus