Constructive innovation of approaching bicyclo[3.2.1]octane in ent-kauranoids

Tetrahedron Letters

Volumn 56, Issue 1, 2015, Pages 23-31

  Zhu, Lili ^a   Huang, Sha Hua ^a,b   Yu, Jing ^a   Hong, Ran ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

^b SHANGHAI INSTITUTE OF TECHNOLOGY   (China)

Author keywords

Biogenesis; Biomimicry; ent Kauranoids; Total synthesis

Indexed keywords

ATRACTYLIGENIN; BICYCLO[3.2.1]OCTANE DERIVATIVE; CAFESTOL; DIMETHYLSHIKOCCIDIN; ENT BEYERANE; ENT KAURENE; GIBBERELLIN A12; GIBBERELLIN DERIVATIVE; ISOSTEVIOL; KAURANE DERIVATIVE; KAURENE DERIVATIVE; KAURENOIC ACID; LONGIKAURIN E; MAOECRYSTAL V; NEOTRIPTERIFORDIN; ORIDONIN A; PLANT GLYCOSIDE; PLANT MEDICINAL PRODUCT; PLATENSIMYCIN; SCULPONEATIN N; SHIKOCCIDIN; STEVIOL; STEVIOL METHYL ESTER; STEVIOSIDE; TERPENE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; BIOGENESIS; CARBOCATION; CHEMICAL MODIFICATION; CHEMICAL REACTION; CLAISEN REARRANGEMENT; COMPUTATIONAL FLUID DYNAMICS; CYCLIZATION; DRUG SYNTHESIS; EXPERIMENTAL DESIGN; HUMAN; IRELAND; MOLECULAR MIMICRY; NONHUMAN; STEREOCHEMISTRY; STEVIA;

EID: 84919469366     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2014.11.035     Document Type: Review

References (80)

1. P. Quitt, E. Mosettig, R.C. Cambie, P.S. Rutledge, and L.H. Briggs J. Am. Chem. Soc. 83 1961 3720
2. H.-D. Sun, S.-X. Huang, and Q.-B. Han Nat. Prod. Rep. 23 2006 673
3. M. Bridel, and R. Lavieille C. R. Hebd. Seances Acad. Sci. 193 1931 72
4. E. Mosettig, and W.R. Nes J. Org. Chem. 20 1955 884
5. H.B. Wood, and H.G. Fletcher J. Am. Chem. Soc. 78 1956 207
6. C. Djerassi, M. Cais, and L.A. Mitscher J. Am. Chem. Soc. 81 1959 2386
7. R.A. Finnegan, and C. Djerassi J. Am. Chem. Soc. 82 1960 4342
8. A.I. Scott, G.A. Sim, G. Ferguson, D.W. Young, and F. McCapra J. Am. Chem. Soc. 84 1962 3197
9. H. Richter, and G. Spiteller Chem. Ber. Recl. 111 1978 3506
10. M. Klingenberg Trends Biochem. Sci. 4 1979 249
11. K. Chen, Q. Shi, T. Fujioka, T. Nakano, C.-Q. Hu, J.-Q. Jin, R.E. Kilkuskie, and K.-H. Lee Biorg. Med. Chem. 3 1995 1345
12. E. Fujita, T. Fujita, H. Katayama, and M. Shibuya Chem. Commun. 1967 252
13. M. Node, N. Ito, I. Uchida, E. Fujita, and K. Fuji Chem. Pharm. Bull. 33 1985 1029
14. K. Fuji, M. Node, N. Ito, E. Fujita, S. Takeda, and N. Unemi Chem. Pharm. Bull. 33 1985 1038
15. T. Fujita, Y. Takeda, and T. Shingu Heterocycles 16 1981 227
16. B.E. Cross, and K. Norton J. Chem. Soc. 1965 1570
17. (b) A personal account, see: L.N. Mander Nat. Prod. Rep. 20 2003 49 and references therein
18. X. Li, J.-X. Pu, Z.-Y. Weng, Y. Zhao, Y. Zhao, W.-L. Xiao, and H.-D. Sun Chem. Biodiv. 7 2010 2888
19. S.-H. Li, J. Wang, X.-M. Niu, Y.-H. Shen, H.-J. Zhang, H.-D. Sun, M.-L. Li, Q.-E. Tian, Y. Lu, P. Cao, and Q.-T. Zheng Org. Lett. 6 2004 4327
20. J. Wang, S.M. Soisson, K. Young, W. Shoop, S. Kodali, A. Galgoci, R. Painter, G. Parthasarathy, Y.S. Tang, R. Cummings, S. Ha, K. Dorso, M. Motyl, H. Jayasuriya, J. Ondeyka, K. Herath, C.W. Zhang, L. Hernandez, J. Allocco, A. Basilio, J.R. Tormo, O. Genilloud, F. Vicente, F. Pelaez, L. Colwell, S.H. Lee, B. Michael, T. Felcetto, C. Gill, L.L. Silver, J.D. Hermes, K. Bartizal, J. Barrett, D. Schmatz, J.W. Becker, D. Cully, and S.B. Singh Nature 441 2006 358
21. M.-H. Filippini, and J. Rodriguez Chem. Rev. 99 1999 27
22. M. Presset, Y. Coquerel, and J. Rodriguez Chem. Rev. 113 2013 525
23. K.E. Lazarski, B.J. Moritz, and R.J. Thomson Angew. Chem., Int. Ed. 53 2014 10588
24. K. Tiefenbacher, and J. Mulzer Angew. Chem., Int. Ed. 47 2008 2548
25. Y.-S. Yao, and Z.-J. Yao Chin. J. Org. Chem. 28 2008 1553
26. K. Palanichamy, and K.P. Kaliappan Chem. Asian J. 5 2010 668
27. M. Saleem, H. Hussain, I. Ahmed, T. van Ree, and K. Krohn Nat. Prod. Rep. 28 2011 1534
28. R.A. Bell, R.E. Ireland, and R.A. Pastyka J. Org. Chem. 47 1962 3741
29. R.F. Church, R.E. Ireland, and J.A. Marshall Tetrahedron Lett. 1 1960 l
30. R.A. Bell, R.E. Ireland, and R.A. Partyka J. Org. Chem. 31 1966 2530
31. R.F. Church, R.E. Ireland, and J.A. Marshall J. Org. Chem. 31 1966 2526
32. C.A. Henrick, and P.R. Jefferies Aust. J. Chem. 17 1964 915
33. M. Katsumi, B.O. Phinney, P.R. Jefferies, and C.A. Henrick Science 144 1964 849
34. K. Mori, and M. Matsui Tetrahedron Lett. 2 1966 175
35. K. Mori, M. Matsui, N. Ikekawa, and Y. Sumiki Tetrahedron Lett. 29 1966 3395
36. E. Mosettig, U. Beglinger, F. Dolder, H. Lichti, P. Quitt, and J.A. Waters J. Am. Chem. Soc. 85 1963 2305
37. M. Ruddat, A. Lang, and E. Mosettig Naturwissenschaften 50 1963 23
38. K. Mori, Y. Nakahara, and M. Matsui Tetrahedron Lett. 11 1970 2411
39. Y. Nakahara, K. Mori, and M. Matsui Agric. Biol. Chem. 35 1971 918
40. K. Mori, Y. Nakahara, and M. Matsui Tetrahedron 28 1972 3217
41. F.E. Ziegler, and J.A. Kloek Tetrahedron 33 1977 373
42. F.E. Ziegler, and J.A. Kloek Tetrahedron Lett. 12 1971 2201
43. J.A. Hogg J. Am. Chem. Soc. 70 1948 161
44. E.C. Cherney, J.C. Green, and P.S. Baran Angew. Chem., Int. Ed. 52 2013 9019
45. B.B. Snider, J.Y. Kiselgof, and B.M. Foxman J. Org. Chem. 63 1998 7945
46. B.B. Snider Tetrahedron 65 2009 10738
47. W.W. Huber, G. Scharf, G. Nagel, S. Prustomersky, R. Schulte-Hermann, and B. Kaina Mut. Res. 522 2003 57
48. S.E. George, K. Ramalakshmi, and L.J. Mohan Rao Crit. Rev. Food Sci. Nutr. 48 2008 464
49. S.T.J. van Cruchten, L.H.J. de Haan, P.P.J. Mulder, C. Kunne, M.V. Boekschoten, M.B. Katan, J.M.M.J.G. Aarts, and R.F. Witkamp J. Nutr. Biochem. 21 2010 757
50. K.-A. Lee, J.-I. Chae, and J.-H. Shim J. Biomed. Sci. 19 2012 60
51. E.J. Corey, G. Wess, Y.B. Xiang, and A.K. Singh J. Am. Chem. Soc. 109 1987 4717
52. A.K. Singh, R.K. Bakshi, and E.J. Corey J. Am. Chem. Soc. 109 1987 6187
53. E.J. Corey, A. GuzmanPerez, and S.E. Lazerwith J. Am. Chem. Soc. 119 1997 11769
54. E.J. Corey, and K. Liu J. Am. Chem. Soc. 119 1997 9929
55. L. Zhu, J. Luo, and R. Hong Org. Lett. 16 2014 2162
56. L. Zhu, and R. Hong Chin. J. Chem. 31 2013 111
57. T. Ikezoe, Y. Yang, K. Bandobashi, T. Saito, S. Takemoto, H. Machida, K. Togitani, H.P. Koeffler, and H. Taguchi Mol. Cancer. Ther. 4 2005 578
58. H.L. Huang, H.Y. Weng, L.Q. Wang, C.H. Yu, Q.J. Huang, P.P. Zhao, J.Z. Wen, H. Zhou, and L.H. Qu Mol. Cancer. Ther. 11 2012 1155
59. F.H. Gao, F. Liu, W. Wei, L.B. Liu, M.H. Xu, Z.Y. Guo, W. Li, B. Jiang, and Y.L. Wu Int. J. Mol. Med. 29 2012 649
60. S. Wang, Z. Zhong, J. Wan, W. Tan, G. Wu, M. Chen, and Y. Wang Am. J. Chin. Med. 41 2013 177
61. R. Bao, Y. Shu, X. Wu, H. Weng, Q. Ding, Y. Cao, M. Li, J. Mu, W. Wu, Q. Ding, Z. Tan, T. Liu, L. Jiang, Y. Hu, J. Gu, and Y. Liu BMC Cancer 14 2014 217
62. H. Weng, H. Huang, B. Dong, P. Zhao, H. Zhou, and L. Qu Cancer Res. 74 2014 4409
63. W.S. Zhou, and Y.X. Cheng Sci. China Ser. B Chem. 35 1992 194
64. D. Backhaus, and L.A. Paquette Tetrahedron Lett. 38 1997 29
65. L.A. Paquette, D. Backhaus, and R. Braun J. Am. Chem. Soc. 118 1996 11990
66. L.A. Paquette, and G. Ladouceur J. Org. Chem. 54 1989 4278
67. P. Wieland, and K. Miescher Helv. Chim. Acta 33 1950 2215
68. M. Toyota, T. Wada, and K. Fukumoto Heterocycles 41 1995 1135
69. M. Toyota, T. Wada, Y. Nishikawa, K. Yanai, K. Fukumoto, and C. Kabuto Tetrahedron 51 1995 6927
70. M. Toyota, T. Wada, and M. Ihara J. Org. Chem. 65 2000 4565
71. J.T.S. Yeoman, V.W. Mak, and S.E. Reisman J. Am. Chem. Soc. 135 2013 11764
72. J.T.S. Yeoman, J.Y. Cha, V.W. Mak, and S.E. Reisman Tetrahedron 70 2014 4070
73. F. Wenkert Chem. Ind. (London) 1955 282
74. P.M. Dewick Medicinal Natural Products: A Biosynthetic Approach 3rd ed. 2009 John Wiley & Sons New York 223
75. The nonclassic 2-norbornyl cation was recently resolved by X-ray crystallography, see: F. Scholz, D. Himmel, F.W. Heinemann, P.V.R. Schleyer, K. Meyer, and I. Krossing Science 341 2013 62
76. Y.J. Hong, and D.J. Tantillo J. Am. Chem. Soc. 132 2010 5375
77. Y. Gao, R.B. Honzatko, and R.J. Peters Nat. Prod. Rep. 29 2012 1153
78. K. Zhou, and R.J. Peters Chem. Commun. 2011 4074
79. A.J. Jackson, D.M. Hershey, T. Chesnut, M. Xu, and R.J. Peters Phytochemistry 103 2014 13
80. H. Oikawa, K. Nakamura, H. Toshima, T. Toyomasu, and T. Sassa J. Am. Chem. Soc. 124 2002 9145