Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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Syntheses of Morindaparvin A and Its Derivatives

  • Rho, Young-S. (Dept. of Chemistry, Chonbuk National University) ;
  • Park, Si-Ho (Research & Development Center, Miwon Co., Ltd.) ;
  • Kim, Sung-Lyeol (Research & Development Center, Miwon Co., Ltd.) ;
  • Yun, Yeo-Keun (Research & Development Center, Miwon Co., Ltd.) ;
  • Cho, In-Ho (Research & Development Center, Miwon Co., Ltd.) ;
  • Kang, Heun-Soo (Research & Development Center, Miwon Co., Ltd.)
  • Published : 1994.05.20
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Abstract

A general route for convergent syntheses of morindaparvin derivatives with 1,2-methylene-dioxyanthraquinone pattern is described. The anion of 2-methoxycyclohexanone (3), generated with lithium cyclohexylisopropylamine at -78 $^{\circ}C$, was sulfenylated with phenyl phenylthiosulfonate followed by elimination to afford ${\alpha},\;{\beta}$ -unsaturated carbonyl system 8. 6-Methoxy-2-cyclohexen-l-one (8) was condensed with the four phthalide sulfones derivatives 10a-d, to provide morindaparvin derivatives, 1a-d.

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References

  1. Flora of Taiwan v.IV Li, H. L.;Liu, T. S.;Huang, T. C.;Koyama, T.;DeVol, C. E.
  2. Chung Yao Ta Tzutien v.I
  3. Naturally Occurring Ouinones Thomson, R. H.
  4. Pharmaceutical Bontany Kan, W. S.
  5. J. Nat. Prod. v.45 Chang, P.;Lee, K-H.;Shingu, T.;Hirayama,T.;Hall, I. H.
  6. J. Nat. Prod. v.48 Chang, P.;Lee, K-H.
  7. J. Nat. Prod. v.44 Lee, K. H.;Tagahara, K.;Suzuki, H.;Wu, R. Y.;Haruna, M.;Hall,I. H.;Huang, H. C.;Iida, T.;Lai, J. S.
  8. Cancer Therapy in Mordern China Sugi, M.;Nagashio, Y.;Kondo, K.(Ed.)
  9. J. Nat. Prod. v.52 Khanapure, S. P.;Biehl, E. R.
  10. J. Eco. Entomol. v.66 Desmarchelier, J.;Krieger, R. I.;Lee, P. W.;Fukuto, T. R.
  11. J. Org. Chem. v.54 Hauser, F. M.;Hewawasam, P.;Rho, Y. S.
  12. J. Org. Chem. v.43 Hauser, F. M.;Rhee, R. P.
  13. J. Kor. Chem. Soc. v.37 Rho, Y. S.;Cho. I. H.;Park, S. H.;Ahn, K. H.
  14. Organic Syntheses v.IV Allingger, N. L.;Rabjohn, N.(ed.)
  15. J. Am. Chem. Soc. v.97 Reich, H. J.;Renga, J. M.;Reich, I. L.
  16. Tetrahedron Lett. Ryu, I.;Murai, S.;Hatayama, Y.;Sonoda, N.
  17. J. Org. Chem. v.43 Rubottom, G. M.;Gruber, J. M.
  18. J. Am. Chem. Soc. v.98 Trost, B. M.;Salzmann, T. N.;Hiroi, K.
  19. J. Am. Chem. Soc. v.95 Trost, B. M.;Salzmann, T. N.
  20. J. Am. Chem. Soc. v.99 Trost, B. M.;Massiot, G. S.
  21. J. Org. Chem. v.32 Shine, H. J.;Rahman, M.;Seeger, H.;Wu, G. S.
  22. J. Chem. Soc. Davis, B. R.;Halsall, T. G.
  23. J. Org. Chem. v.57 Ishizaki, M.;Hoshino, O.;Iitaka, Y.
  24. J. Chem. Soc. Burn, D.;Petrow, V.
  25. J. Org. Chem. v.38 Stotter, P. L.;Hill, K. A.
  26. J. Org. Chem. v.30 Garbisch, Jr. E. W.
  27. Synthesis Fleming, I.;Paterson, I.
  28. Tetrahedron v.40 Hauser, F. M.;Prasanna, S.
  29. Tetrahedron Lett. v.36 Grieco, P. A.;Reap, J. P.
  30. Tetrahedron Lett. v.21 Williard, P. G.;Fryhle, C. B.
  31. Tetrahedron Lett. v.38 Clark, J. H.;Holland, H. L.;Miller, J. M.

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