Total syntheses of lindenane-type sesquiterpenoids: (±)- chloranthalactones A, B, F, (±)-9-hydroxy heterogorgiolide, and (±)-shizukanolide e

Tetrahedron

Volumn 68, Issue 47, 2012, Pages 9624-9637

  Yue, Guizhou ^a,c   Yang, Li ^a   Yuan, Changchun ^a   Du, Biao ^a   Liu, Bo ^a,b  

^a Sichuan University   (China)

^b SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

^c SICHUAN AGRICULTURAL UNIVERSITY   (China)

Author keywords

Alkylidenebutenolide cyclization; Hodgson cyclopropanation; Lindenane type sesquiterpenoid; Matteson epoxidation; Total synthesis

Indexed keywords

9 HYDROXY HETEROGORGIOLIDE; BUTENOLIDE; CHLORANTHALACTONE A; CHLORANTHALACTONE B; CHLORANTHALACTONE C; KETONE; SESQUITERPENOID; SHIZUKANOLIDE E; UNCLASSIFIED DRUG;

ARTICLE; CYCLOPROPANATION; DRUG ISOLATION; DRUG SYNTHESIS; EPOXIDATION; METHODOLOGY; PRIORITY JOURNAL; RACEMIC MIXTURE; STEREOCHEMISTRY;

CHLORANTHACEAE;

EID: 84867526791     PISSN: 00404020     EISSN: 14645416     Source Type: Journal    
DOI: 10.1016/j.tet.2012.09.053     Document Type: Article

References (103)

1. C.M. Cao, Y. Peng, Q.W. Shi, and P.G. Xiao Chem. Biodiver. 5 2008 219 238
2. M. Uchida, G. Kusano, Y. Kondo, and S. Nozoe Heterocycles 9 1978 139 144
3. H. Tesso, W.A. Konig, P.T. Son, and P.M. Giang Flavour Fragrance J. 21 2006 592 597
4. B. Wu, S. He, and Y.J. Pan Tetrahedron Lett. 48 2007 453 456
5. M. Uchida, Y. Koike, G. Kusano, Y. Kondo, S. Nozoe, C. Kabuto, and T. Tkaemoto Chem. Pharm. Bull. 28 1980 92 102
6. S. Tahara, Y. Fukiushi, J. Kawabata, and J. Mizutani Agric. Biol. Chem. 45 1981 1511 1512
7. W. Gao, Y. Chen, J. Xie, and S. Zhao Chem. Res. Chin. Univ. 8 1987 141 142
8. G. Kusano, M. Abe, Y. Koike, M. Uchida, S. Nozoe, and Z. Taira Yakugaku Zasshi 111 1991 756 764
9. Y. Takeda, H. Yamashita, T. Matsumoto, and H. Terao Phytochemistry 33 1993 713 715
10. H. Okamura, T. Iwagawa, and M. Nakatani Bull. Chem. Soc. Jpn. 68 1995 3465 3467
11. W.Y. Tsui, and G.D. Brown Phytochemistry 43 1996 819 821
12. F. Wang, S.T. Yuan, and D.N. Zhu Chin. J. Nat. Med. 5 2007 174 178
13. X.C. Wang, W.Q. Wu, S.P. Ma, J.H. Liu, and L.H. Hu Chin. J. Nat. Med. 6 2008 404 407
14. J. Kawabata, S. Tahara, J. Mizutani, A. Furusaki, N. Hashiba, and T. Matsunoto Agric. Biol. Chem. 43 1979 885 887
15. J. Kawabata, S. Tahara, and J. Mizutani Agric. Biol. Chem. 45 1981 1447 1453
16. J. Kawabata, and J. Mizutani Agric. Biol. Chem. 52 1988 2965 2966
17. J. Kawabata, and J. Mizutani Agric. Biol. Chem. 53 1989 203 207
18. C. Li, D. Zhang, and Y. Luo Acta Pharm. Sin. 40 2005 525 528
19. X.C. Wang, L.L. Wang, X.W. Ouyang, S.P. Ma, J.H. Liu, and L.H. Hu Helv. Chim. Acta 92 2009 313 320
20. C. Wang, L. Zhu, J. Yang, C. Li, and D. Zhang Chinese J. Chinese Materia Medica 35 2010 714 716
21. P.-L. Fang, H.-Y. Liu, and H.-M. Zhong Chin. J. Nat. Med. 10 2012 24 27
22. J.E. Heo, J.L. Jin, Y.Y. Lee, and H.S. Yun-Choi Nat. Prod. Sci. 11 2005 41 45
23. F. Bohlmann, C. Zdero, R.M. King, and H. Robinson Phytochemistry 19 1980 689 691
24. M. Bittner, J. Jakupovic, F. Bohlmann, and M. Silva Phytochemistry 28 1989 271 273
25. H. Okamura, N. Nakashima, T. Iwagawa, N. Nakayama, and M. Nakatani Chem. Lett. 1994 1541 1542
26. C.F. Zhang, N. Nakamura, S. Tewtrakul, M. Hattori, Q.S. Sun, Z.T. Wang, and T. Fujiwara Chem. Pharm. Bull. 50 2002 1195 1200
27. W. Zhang, Y.W. Guo, E. Mollo, and G. Cimino Chin. J. Nat. Med. 1 2003 13 15
28. H.X. Kuang, Y.G. Xia, B.Y. Yang, Q.H. Wang, and S.W. Lu Chem. Biodiversity 5 2008 1736 1742
29. X.R. Hu, J.S. Yang, and X.D. Xu Chem. Pharm. Bull. 57 2009 418 420
30. L. Acebey, V. Jullian, D. Sereno, S. Chevalley, Y. Estevez, C. Moulis, S. Beck, A. Valentin, A. Gimenez, and M. Sauvain Planta Med. 76 2010 365 368
31. Q.H. Wang, H.X. Kuang, B.Y. Yang, Y.G. Xia, J.S. Wang, and L.Y. Kong J. Nat. Prod. 74 2011 16 20
32. S.Y. Kao, J.H. Su, T.L. Hwang, J.H. Sheu, Z.H. Wen, Y.C. Wu, and P.J. Sung Mar. Drugs 9 2011 1534 1542
33. S.Y. Kao, J.H. Su, T.L. Hwang, J.H. Sheu, Y.D. Su, C.S. Lin, Y.C. Chang, W.H. Wang, L.S. Fang, and P.J. Sung Tetrahedron 67 2011 7311 7315
34. J. Kawabata, Y. Fukushi, S. Tahara, and J. Mizutani Phytochemistry 29 1990 2332 2334
35. J. Kawabata, and J. Mizutani Phytochemistry 31 1992 1293 1296
36. J. Kawabata, E. Fukushi, and J. Mizutani Phytochemistry 39 1995 121 125
37. J. Kawabata, E. Funkushi, and J. Mizutani Phytochemistry 47 1998 231 235
38. X.C. Wang, Y.N. Zhang, L.L. Wang, S.P. Ma, J.H. Liu, and L.H. Hu J. Nat. Prod. 71 2008 674 677
39. S.P. Yang, and J.M. Yue Tetrahedron Lett. 47 2006 1129 1132
40. Y.J. Xu, C.P. Tang, C.Q. Ke, J.B. Zhang, H.C. Weiss, E.R. Gesing, and Y. Ye J. Nat. Prod. 70 2007 1987 1990
41. S. Yang, Z. Gao, F. Wang, S. Liao, H. Chen, C. Zhang, G. Hu, and J. Yue Org. Lett. 9 2007 903 906
42. S.P. Yang, Z.B. Gao, Y. Wu, G.Y. Hu, and J.M. Yue Tetrahedron 64 2008 2027 2034
43. S.-Y. Kim, Y. Kashiwada, K. Kawazoe, K. Murakami, H.-D. Sun, S.-L. Li, and Y. Takaishi Phytochem. Lett. 2 2009 110 113
44. S.Y. Kim, Y. Kashiwada, K. Kawazoe, K. Murakami, H.D. Sun, S.L. Li, and Y. Takaishi Tetrahedron Lett. 50 2009 6032 6035
45. S.-Y. Kim, Y. Kashiwada, K. Kawazoe, K. Murakami, H.-D. Sun, S.-L. Li, and Y. Takaishi Chem. Pharm. Bull. 10 2011 1281 1284
46. L. Acebey, M. Sauvain, S. Beck, C. Moulis, A. Gimenez, and V. Jullian Org. Lett. 9 2007 4693 4696
47. P.L. Fang, Y.L. Cao, H. Yan, L.L. Pan, S.C. Liu, N.B. Gong, Y. Lu, C.X. Chen, H.M. Zhong, Y. Guo, and H.Y. Liu J. Nat. Prod. 74 2011 1408 1413
48. G.Y. Lian, and B.A. Yu Chem. Biodiversity 7 2010 2660 2691
49. Z.-J. Zhan, Y.-M. Ying, L.-F. Ma, and W.-G. Shan Nat. Prod. Rep. 28 2011 594 629
50. X.-F. He, S. Zhang, R.-X. Zhu, S.-P. Yang, T. Yuan, and J.-M. Yue Tetrahedron 67 2011 3170 3174
51. M. Zhang, M. Iinuma, J.-S. Wang, M. Oyama, T. Ito, and L.-Y. Kong J. Nat. Prod. 75 2012 694 698
52. Y. Li, D.M. Zhang, J.B. Li, S.S. Yu, and L. Yong-Ming J. Nat. Prod. 69 2006 616 620
53. O.E. Kwon, H.S. Lee, S.W. Lee, K. Bae, K. Kim, M. Hayashi, M.C. Rho, and Y.K. Kim J. Ethnopharmacol. 104 2006 270 277
54. S.W. Kwon, Y.K. Kim, H.S. Ryu, H.K. Lee, J.S. Kang, H.M. Kim, J.T. Hong, Y. Kim, and S.B. Han Biomol. Ther. 19 2011 59 64
55. S.B. Jones, B. Simmons, A. Mastracchio, and D.W.C. MacMillan Nature 475 2011 183 188
56. T.W. Fenolon, D. Schwaebisch, A.V.W. Mayweg, V. Lee, R.M. Adlington, and J.E. Baldwin Synlett 2007 2679 2682 For studies on the total synthesis of chlorahololide A, see
57. Y. Liu, and F.J. Nan Tetrahedron Lett. 51 2010 1374 1376
58. S. Qian, and G. Zhao Synlett 2011 722 724
59. Y.S. Lu, and X.S. Peng Org. Lett. 13 2011 2940 2943
60. G. Yue, L. Yang, C. Yuan, X. Jiang, and B. Liu Org. Lett. 13 2011 5406 5408
61. S. Qian, and G. Zhao Chem. Commun. 2012 3530 3532
62. M. Huang, C. Huang, and B. Liu Tetrahedron Lett. 50 2009 2797 2800
63. J. Huang, X. Huang, and B. Liu Org. Biomol. Chem. 8 2010 2697 2699
64. D. Yang, J. Huang, and B. Liu Eur. J. Org. Chem. 2010 2010 4185 4188
65. Y. Chen, J. Huang, and B. Liu Tetrahedron Lett. 51 2010 4655 4657
66. C. Huang, and B. Liu Chem. Commun. 2010 5280 5282
67. M. Huang, L. Song, and B. Liu Org. Lett. 12 2010 2504 2507
68. C. Huang, W. Zhang, and B. Liu Sci. China: Chem. 54 2011 43 55
69. Y. Liu, C. Huang, and B. Liu Tetrahedron Lett. 52 2011 5802 5804
70. H.L. Gordon, S. Freeman, and T. Hudlicky Synlett 2005 2911 2914
71. D.M. Hodgson, Y.K. Chung, and J.-M. Paris J. Am. Chem. Soc. 126 2004 8664 8665
72. D.M. Hodgson, Y.K. Chung, and J.M. Paris Synthesis 2005 2264 2266
73. D.M. Hodgson, Y.K. Chung, I. Nuzzo, G. Freixas, K.K. Kulikiewicz, E. Cleator, and J.-M. Paris J. Am. Chem. Soc. 129 2007 4456 4462
74. A.D. Alorati, M.M. Bio, K.M.J. Brands, E. Cleator, A.J. Davies, R.D. Wilson, and C.S. Wise Org. Process Res. Dev. 11 2007 637 641
75. D.M. Hodgson, and S. Salik Synlett 2009 1730 1732
76. D.M. Hodgson, S. Salik, and D.J. Fox J. Org. Chem. 75 2010 2157 2168
77. T. Stellfeld, U. Bhatt, and M. Kalesse Org. Lett. 6 2004 3889 3892
78. T. Kametani, M. Tsubuki, and H. Nemoto J. Org. Chem. 45 1980 4391 4398
79. D.B. Ramachary, K. Ramakumar, and V.V. Narayana J. Org. Chem. 72 2007 1458 1463
80. S. Katsumura, A. Kimura, and S. Isoe Tetrahedron 45 1989 1337 1346
81. L.R. Zehnder, L.-L. Wei, R.P. Hsung, K.P. Cole, M.J. McLaughlin, H.C. Shen, H.M. Sklenicka, J. Wang, and C.A. Zificsak Org. Lett. 3 2001 2141 2144
82. CCDC 857170 contains the supplementary crystallographic data for compound 11. These data can be obtained free of charge from the Cambridge Crystallographic Data Centre via www: ccdc.cam. ac.uk/data-request/cif.
83. L.H.D. Jenniskens, and A.D. Groot Tetrahedron 54 1998 5617 5622
84. E.J. Corey, and B. Hopkins Tetrahedron Lett. 23 1982 1979 1982
85. K.C. Nicolaou, Y.-P. Sun, X.-S. Peng, D. Polet, and D.Y.-K. Chen Angew. Chem., Int. Ed. 47 2007 7310 7313
86. M. Ori, N. Toda, K. Takami, K. Tago, and H. Kogen Tetrahedron 61 2005 2075 2104
87. T.J. Michnick, and D.S. Matteson Synlett 1991 631 632
88. E.J. Corey, and R.A.E. Winter J. Am. Chem. Soc. 85 1963 2677 2678
89. J. Andersch, and M. Bols Chem. - Eur. J. 7 2001 3744 3747
90. E. Negishi, and M. Kotora Tetrahedron 53 1997 6707 6738
91. R. Brückner Chem. Commun. 2001 141 152
92. R. Brückner Curr. Org. Chem. 5 2001 679 718
93. For a recent example, see: W.H. Xu, J.F. Wang, G.Z. Liu, G.F. Hong, and H.M. Liu Org. Biomol. Chem. 5 2007 1247 1250
94. For a recent example, see: S. Inack-Ngi, R. Rahmani, L. Commeiras, G. Chouraqui, J. Thibonnet, A. Duchene, M. Abarbri, and J.L. Parrain Adv. Synth. Catal. 351 2009 779 788
95. For the application of para-toluenesulfonic acid, see: R. Nagase, M. Katayama, H. Mura, N. Matsuo, and Y. Tanabe Tetrahedron Lett. 49 2008 4509 4512
96. For the application of phosphorus tribromide, see: A. Armstrong, T.J. Critchley, M.-E. Gourdol-Martin, R.D. Kelsey, and A.A. Mortlock J. Chem. Soc., Perkin Trans. 1 2002 1344 1350
97. For the application of hydrogen chloride, see: L. Baiocchi, M. Bonanomi, M. Giannangeli, and G. Picconi Synthesis 1979 434 436
98. For the application of phosphorus pentoxide-methanesulfonic acid, see: A.G. Schultz, and Y.K. Yee J. Org. Chem. 41 1976 561 563
99. K.S. Kochhar, D.A. Cottrell, and H.W. Pinnick Tetrahedron Lett. 24 1983 1323 1326
100. W.M. Doane, B.S. Shasha, C.R. Russell, and C.E. Rist J. Org. Chem. 30 1965 3071 3075
101. Y. Kiyotsuka, H.P. Acharya, Y. Katayama, T. Hyodo, and Y. Kobayashi Org. Lett. 10 2008 1719 1722
102. A.B. Theis, and C.A. Townsend Synth. Commun. 11 1981 157 166
103. R.L. Danheiser, K.R. Romines, H. Koyama, S.K. Gee, C.R. Johnson, and J.R. Medich Org. Synth. 71 1993 133 137