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Journal of Chemistry
Volume 2017, Article ID 3971253, 11 pages
https://doi.org/10.1155/2017/3971253
Research Article

Bioactive Phytochemicals: Efficient Synthesis of Optically Active Substituted Flav-3-enes and Flav-3-en-3-o-R Derivatives

1Faculty of Natural Sciences, Mangosuthu University of Technology, Umlazi, Durban, KwaZulu-Natal, South Africa
2Department of Agriculture, Faculty of Health and Environmental Sciences, Central University of Technology, Free State, 1 Park Road, Bloemfontein 9301, South Africa

Correspondence should be addressed to Matthew Chilaka Achilonu; az.ca.tum@wehttam.unolihca

Received 21 December 2016; Accepted 7 March 2017; Published 18 May 2017

Academic Editor: Bin Yu

Copyright © 2017 Matthew Chilaka Achilonu et al. 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. H. L. Min, T. C. Eui, M. L. Yoon, D. Kim, and S. P. Yong, “Stereoselective syntheses of 3-substituted flavene derivatives and asymmetric dehydration via kinetic resolution,” Bulletin of the Korean Chemical Society, vol. 29, no. 7, pp. 1299-1300, 2008. View at Publisher · View at Google Scholar · View at Scopus
  2. C.-W. Lee, H.-J. Choi, H.-S. Kim et al., “Biflavonoids isolated from Selaginella tamariscina regulate the expression of matrix metalloproteinase in human skin fibroblasts,” Bioorganic & Medicinal Chemistry, vol. 16, pp. 732–738, 2008. View at Publisher · View at Google Scholar
  3. X. Zheng, W.-D. Meng, and F.-L. Qing, “Synthesis of gem-difluoromethylenated biflavonoid via the Suzuki coupling reaction,” Tetrahedron Letters, vol. 45, no. 43, pp. 8083–8085, 2004. View at Publisher · View at Google Scholar · View at Scopus
  4. B. Gil, M. J. Sanz, M. C. Terencio, R. Gunasegaran, M. Paya, and M. J. Alcaraz, “Morelloflavone, a novel biflavonoid inhibitor of human secretory phospholipase A, with anti-inflammatory activity,” Biochemical Pharmacology, vol. 53, pp. 733–740, 1997. View at Google Scholar
  5. M. K. Lee, S. W. Lim, H. Yang et al., “Osteoblast differentiation stimulating activity of biflavonoids from Cephalotaxus koreana,” Bioorganic & Medicinal Chemistry Letters, vol. 16, no. 11, pp. 2850–2854, 2006. View at Google Scholar
  6. J. Chen, H. W. Chang, H. P. Kim, and H. Park, “Synthesis of phospholipase A2 inhibitory biflavonoids,” Bioorganic & Medicinal Chemistry Letters, vol. 16, no. 9, pp. 2373–2375, 2006. View at Publisher · View at Google Scholar · View at Scopus
  7. B. C. Das, S. Mohapatra, P. D. Campbell, S. Nayak, S. M. Mahalingam, and T. Evans, “Synthesis of function-oriented 2-phenyl-2H-chromene derivatives using l-pipecolinic acid and substituted guanidine organocatalysts,” Tetrahedron Letters, vol. 51, no. 19, pp. 2567–2570, 2010. View at Publisher · View at Google Scholar · View at Scopus
  8. M. C. Achilonu and D. O. Umesiobi, “The formation of carbon–carbon and carbon–heteroatom bonds using silver tetrafluoroborate as a promoter,” Arabian Journal of Chemistry, vol. 9, supplement 2, pp. S1984–S2003, 2016. View at Publisher · View at Google Scholar
  9. M. C. Achilonu and D. O. Umesiobi, “Bioactive phytochemicals: bioactivity, sources, preparations, and/or modifications via silver tetrafluoroborate mediation,” Journal of Chemistry, vol. 2015, Article ID 629085, 22 pages, 2015. View at Google Scholar
  10. S. Guillotin, P. Sanoner, and C. M. G. C. Renard, “Stabilisation of the colour of anthocyanins in solutions by admixture with phytocomponents from apple,” Journal of Horticultural Science & Biotechnology ISAFRUIT Special Issue, pp. 96–99, 2009. View at Google Scholar
  11. J. W. Clark-Lewis and M. I. Baig, “Flavan derivatives. XXXII. Structures and N.M.R. spectra of flav-2-enes and flav-3-enes; hydroboration and hydroxylation of flav-3-enes,” Australian Journal of Chemistry, vol. 24, no. 12, pp. 2581–2592, 1971. View at Publisher · View at Google Scholar · View at Scopus
  12. G. A. Iacobucci and J. G. Sweeny, “The chemistry of anthocyanins, anthocyanidins and related flavylium salts,” Tetrahedron, vol. 39, no. 19, pp. 3005–3038, 1983. View at Publisher · View at Google Scholar · View at Scopus
  13. L. Jurd, “Structural and Functional Aspects of Phytochemistry,” in Recent progress in Chemistry of Flavylium Salts, V. C. Rumeckles and T. C. Tso, Eds., vol. 5, pp. 135–142, Academic Press, New York, NY, USA, 1972. View at Google Scholar
  14. J. W. Clark-Lewis and R. W. Jemison, “Flavan derivatives. XXVIII. Stereochemistry of products synthesized from flav-3-enes and flavanones,” Australian Journal of Chemistry, vol. 23, no. 2, pp. 315–321, 1970. View at Publisher · View at Google Scholar · View at Scopus
  15. N. T. Zaveri, “Synthesis of a 3,4,5-trimethoxybenzoyl ester analogue of epigallocatechin-3-gallate (EGCG): a potential route to the natural product green tea catechin, EGCG,” Organic Letters, vol. 3, no. 6, pp. 843–845, 2001. View at Publisher · View at Google Scholar · View at Scopus
  16. A. Pelter and P. Stainton, “The mass spectra of oxygen heterocycles. Part (V). The mass spectra of 2′-hydroxyflavonoids,” Journal of the Chemical Society C: Organic Chemistry, pp. 1933–1937, 1967. View at Publisher · View at Google Scholar · View at Scopus
  17. B. Nay, V. Arnaudinaud, J.-F. Peyrat et al., “Total synthesis of isotopically labelled flavonoids, 2: 13C-labelled (±)-catechin from potassium [13C]cyanide,” European Journal of Organic Chemistry, no. 7, pp. 1279–1283, 2000. View at Publisher · View at Google Scholar · View at Scopus
  18. M. Deodhar, D. S. Black, and N. Kumar, “Acid catalyzed stereoselective rearrangement and dimerization of flavenes: synthesis of dependensin,” Tetrahedron, vol. 63, no. 24, pp. 5227–5235, 2007. View at Publisher · View at Google Scholar · View at Scopus
  19. G. Casiraghi and G. Casnati, “A new method for the synthesis of flav-2-enes,” Journal of the Chemical Society D: Chemical Communications, vol. 5, p. 321, 1970. View at Google Scholar
  20. G. Cardillo, R. Cricchio, and L. Merlini, “Biogenetic-like synthesis of flav-3-enes from o-cinnamylphenols,” Tetrahedron Letters, vol. 10, no. 12, pp. 907-908, 1969. View at Publisher · View at Google Scholar · View at Scopus
  21. R. S. Subramanian and K. K. Balasubramanian, “A novel synthesis of flav-3-enes by claisen rearrangement,” Tetrahedron Letters, vol. 29, no. 51, pp. 6797–6799, 1988. View at Publisher · View at Google Scholar · View at Scopus
  22. M. C. Achilonu, S. L. Bonnet, and J. H. van der Westhuizen, “Synthesis of proanthocyanidins. Part 1. The first oxidative formation of the interflavanyl bond in procyanidins,” Organic Letters, vol. 10, no. 17, pp. 3865–3868, 2008. View at Publisher · View at Google Scholar · View at Scopus
  23. A. P. Kozikowski, W. Tückmantel, and C. George, “Studies in polyphenol chemistry and bioactivity. 2. Establishment of interflavan linkage regio- and stereochemistry by oxidative degradation of an O-alkylated derivative of procyanidin B2 to (R)-(−)-2,4-diphenylbutyric acid,” Journal of Organic Chemistry, vol. 65, no. 17, pp. 5371–5381, 2000. View at Google Scholar
  24. J. F. O'Connell and H. Rapoport, “1-Benzenesulfonyl- and 1-p-toluenesulfonyl-3-methylimidazolium triflates: efficient reagents for the preparation of arylsulfonamides and arylsulfonates,” Journal of Organic Chemistry, vol. 57, no. 17, pp. 4775–4777, 1992. View at Publisher · View at Google Scholar · View at Scopus
  25. P. J. Steynberg, J. P. Steynberg, B. C. B. Bezuidenhoudt, and D. Ferreira, “Oligomeric flavanoids. Part 19. Reductive cleavage of the interflavanyl bond in proanthocyanidins,” Journal of the Chemical Society, Perkin Transactions 1, no. 23, pp. 3005–3012, 1995. View at Publisher · View at Google Scholar · View at Scopus
  26. D. Jacques, C. T. Opie, L. J. Porter, and E. Haslam, “Plant proanthocyanidins. Part 4. Biosynthesis of procyanidins and observations on the metabolism of cyanidin in plants,” Journal of the Chemical Society, Perkin Transactions 1, no. 14, pp. 1637–1643, 1977. View at Publisher · View at Google Scholar · View at Scopus
  27. J. Coetzee, E. Malan, and D. Ferreira, “Synthesis and reactions of flav-3-en-3-ols,” Tetrahedron, vol. 56, no. 13, pp. 1819–1824, 2000. View at Publisher · View at Google Scholar · View at Scopus