Natural Products and Bioprospecting ›› 2015, Vol. 5 ›› Issue (5): 255-261.DOI: 10.1007/s13659-015-0073-3
• Original article • Previous Articles Next Articles
Qi-Long Zhou1, Hui-Jing Wang1, Pei Tang1, Hao Song2, Yong Qin2
Received:
2015-09-03
Revised:
2015-09-22
Online:
2018-02-11
Published:
2015-10-24
Supported by:
Qi-Long Zhou1, Hui-Jing Wang1, Pei Tang1, Hao Song2, Yong Qin2
通讯作者:
Pei Tang,e-mail:tangpei@cqu.edu.cn;Yong Qin,e-mail:yongqin@scu.edu.cn
基金资助:
Qi-Long Zhou, Hui-Jing Wang, Pei Tang, Hao Song, Yong Qin. Total Synthesis of Lignan Lactone(-)-Hinokinin[J]. Natural Products and Bioprospecting, 2015, 5(5): 255-261.
Qi-Long Zhou, Hui-Jing Wang, Pei Tang, Hao Song, Yong Qin. Total Synthesis of Lignan Lactone(-)-Hinokinin[J]. 应用天然产物, 2015, 5(5): 255-261.
1. D.C. Ayres, J.D. Loike, in Lignans Chemical, Biological and Clinical Properties (Cambridge University Press, Cambridge, 1990), pp. 12-17 2. R.S. Ward, Chem. Soc. Rev. 11, 75-125 (1982) 3. E. Wenkert, H.E. Gottlieb, O.R. Gottlieb, M.O.S. Pereira, M.D. Formiga, Phytochemistry 15, 1547-1551 (1976) 4. P.V. Kiem, C.V. Minh, N.T. Dat, X.F. Cai, J.L. Lee, Y.H. Kim, Arch. Pharm. Res. 26, 1014-1017 (2003) 5. M. Salmoun, J.C. Braekman, Y. Ranarivelo, R. Rasamoelisendra, D. Ralambomanana, J. Dewelle, F. Darro, R. Kiss, Nat. Prod. Res. 21, 111-120 (2007) 6. R.D. Haworth, D. Woodcock, J. Chem. Soc., 1985-1989 (1938) 7. H. Yoda, S. Naito, K. Takabe, N. Tanaka, K. Hosoya, Tetrahedron Lett. 31, 7623-7626 (1990) 8. N. Rehnberg, G. Magnusson, J. Org. Chem. 55, 4340-4349 (1990) 9. J.A. Gaboury, M.P. Sibiand, J. Org. Chem. 58, 2173-2180 (1993) 10. T. Itoh, J. Chika, Y. Takagi, S. Nishiyama, J. Org. Chem. 58, 5717-5723 (1993) 11. T. Honda, N. Kimura, S. Sato, D. Kato, H. Tominaga, J. Chem. Soc., Perkin Trans. 1, 1043-1046 (1994) 12. A. Oeveren, J.F.G.A. Jansen, B.L. Feringa, J. Org. Chem. 59, 5999-6007 (1994) 13. N. Kise, K. Tokioka, Y. Aoyama, J. Org. Chem. 60, 1100-1101 (1995) 14. M.P. Doyle, M.N. Protopopova, Q.L. Zhou, J.W. Bode, J. Org. Chem. 60, 6654-6655 (1995) 15. J.W. Bode, M.P. Doyle, M.N. Protopopova, Q.L. Zhou, J. Org. Chem. 61, 9146-9155 (1996) 16. J. Brinksma, H. Deen, A. Oeveren, B.L. Feringa, J. Chem. Soc., Perkin Trans. 1, 4159-4164 (1998) 17. S. Kamlage, M. Sefkow, B.L. Pool-Zobel, M.G. Peter, Chem. Commun., 331-336 (2001) 18. Y.M. Xia, Q.R. Liang, X.L. Wang, X.P. Cao, X.F. Pan, Chin. J. Chem. 21, 1540-1542 (2003) 19. D.J. Bennett, P.L. Pickering, N.S. Simpkins, Chem. Commun., 1392-1393 (2004) 20. T. Morimoto, H. Nagai, K. Achiwa, Synth. Commun. 35, 857-865 (2005) 21. V.A. Souza, R. Silva, A.C. Pereira, V.A. Royo, J. Saraiva, M. Montanheiro, G.H.B. Souza, A.A.S. Filho, M.D. Grando, P.M. Donate, J.K. Bastos, S. Albuquerque, M.L.A. Silva, Bioorg. Med. Chem. Lett. 15, 303-307 (2005) 22. R. Silva, G.H.B. Souza, A.A. Silva, V.A. Souza, A.C. Pereira, V.A. Royo, M.L.A.E. Silva, P.M. Donate, A.L.S.D. Araujo, J.C.T. Carvalho, J.K. Bastos, Bioorg. Med. Chem. Lett. 15, 1033-1037 (2005) 23. N.B. Carter, R. Mabon, R. Walmsley, A.M.E. Richecoeur, J.B. Sweeney, Synlett, 1747-1749 (2006) 24. R. Kiralj, M.M.C. Ferreira, P.M. Donate, R. Silva, S. Albuquerque, J. Phys. Chem. A 111, 6316-6333 (2007) 25. Y. Xia, J. You, Y. Zhang, Z.J. Su, Chem. Res., 565-569 (2009) 26. K. Yamada, T. Konishi, M. Nakano, S. Fujii, R. Cadou, Y. Yamamoto, K. Tomioka, J. Org. Chem. 77, 5775-5780 (2012) 27. X. Lin, B.R. Switzer, W. Denmark-Wahnefried, Anticancer Res. 21, 3995-3999 (2001) 28. J. Peterson, J. Dwyer, H. Adlercreutz, A. Scalbert, P. Jacques, M.L. McCullough, Nutr. Rev. 68, 571-603 (2010) 29. L. Wilson, M. Friedkin, Biochemistry 6, 3126-3135 (1967) 30. J.K. Kelleher, Mol. Pharm. 13, 232-241 (1977) 31. J.D. Loike, C.F. Brewer, H. Sternlicht, W.J. Gensler, S.B. Horwitz, Cancer Res. 38, 2688-2693 (1978) 32. C.F. Brewer, J.D. Loike, S.B. Horwitz, H. Sternlicht, W.J. Gensler, J. Med. Chem. 22, 215-221 (1979) 33. F. Zavala, D. Guenard, J.P. Robin, E. Brown, J. Med. Chem. 23, 546-549 (1980) 34. P. Potier, Chem. Soc. Rev. 21, 113-119 (1992) 35. X.K. Zhu, J. Guan, Y. Tachibana, K.F. Bastow, S.J. Cho, H.H. Cheng, Y.C. Cheng, M. Gurwith, K.H. Lee, J. Med. Chem. 42, 2441-2446 (1999) 36. K. Tomioka, T. Ishiguro, H. Mizuguchi, N. Komeshima, K. Koga, S. Tsukagoshi, T. Tsuruo, T. Tashiro, S. Tanida, T. Kishi, J. Med. Chem. 34, 54-57 (1991) 37. J.X. Pan, O.D. Hensens, D.L. Zink, M.N. Chang, S.B. Hwang, Phytochemistry 26, 1377-1379 (1987) 38. D.A. Whiting, Nat. Prod. Rep. 2, 191-211 (1985) 39. D.A. Whiting, Nat. Prod. Rep. 4, 499-525 (1987) 40. D.A. Whiting, Nat. Prod. Rep. 7, 349-364 (1990) 41. R.S. Ward, Nat. Prod. Rep. 10, 1-28 (1993) 42. R.S. Ward, Nat. Prod. Rep. 12, 183-205 (1995) 43. R.S. Ward, Nat. Prod. Rep. 14, 43-74 (1997) 44. R.S. Ward, Nat. Prod. Rep. 16, 75-96 (1999) 45. R.S. Ward, Tetrahedron 46, 5029-5041 (1990) 46. R.S. Ward, Synthesis, 719-730 (1992) 47. D. Enders, V. Lausberg, G.D. Signore, O.M. Berner, Synthesis 4, 515-522 (2002) 48. H.J. Wang, P. Tang, Q.L. Zhou, D. Zhang, Z.T. Chen, H.X. Huang, Y. Qin, J. Org. Chem. 80, 2494-2502 (2015) 49. G. Blay, L. Cardona, B. García, L. Lahoz, J. Pedro, Tetrahedron 52, 8611-8618 (1996) 50. O. Yabe, H. Mizufune, T. Ikemoto, Synlett, 1291-1294 (2009) 51. M. Noè, A. Perosa, M. Selva, Green Chem. 15, 2252-2260 (2013) 52. F. Colpaert, S. Mangelinckx, G. Verniest, N.D. Kimpe, J. Org. Chem. 74, 3792-3797 (2009) 53. T. Kochi, J.A. Ellman, J. Am. Chem. Soc. 126, 15652-15653 (2004) 54. T.D. Owens, A.J. Souers, J.A. Ellman, J. Org. Chem. 68, 3-10 (2003) 55. C. Su, Z.C. Chen, Q.G. Zheng, Synthesis, 555-559 (2003) 56. H. Mukherjee, C.A. Martinez, ACS Catal. 1, 1010-1013 (2011) 57. A.P. Krapcho, G.A. Glynn, B.J. Grenon, Tetrahedron Lett. 8, 215-217 (1967) 58. A.P. Krapcho, E.G.E. Jahngen, A.J. Lovey, F.W. Short, Tetrahedron Lett. 15, 1091-1094 (1974) 59. A.P. Krapcho, J.F. Weimaster, J.M. Eldridge, E.G.E. Jahngen, A.J. Lovey, W.P. Stephens, J. Org. Chem. 43, 138-147 (1978) 60. N. Sakai, T. Moriya, T. Konakahara, J. Org. Chem. 72, 5920-5922 (2007) 61. N. Sakai, T. Moriya, K. Fujii, T. Konakahara, Synthesis 21, 3533-3536 (2008) 62. S. Baskaran, S. Chandrasekaran, Tetrahedron Lett. 31, 2775-2778 (1990) 63. S.M. Ali, K. Ramesh, R.T. Borchardt, Tetrahedron Lett. 31, 1509-1512 (1990) |
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