Progress in the total syntheses of trans-Hydrindane-containing terpenoids

Chinese Journal of Organic Chemistry

Volumn 33, Issue 6, 2013, Pages 1167-1185

  Yue, Guizhou ^a,b   Huang, Xuan ^a   Liu, Bo ^a,c  

^a Sichuan University   (China)

^b SICHUAN AGRICULTURAL UNIVERSITY   (China)

^c SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

Terpenoids; Total synthesis; Trans hydrindane

Indexed keywords

EID: 84880463343     PISSN: 02532786     EISSN: None     Source Type: Journal    
DOI: 10.6023/cjoc201303047     Document Type: Review

References (83)

1. Roberts J. S. Nat. Prod. Rep. 1985 2 97.
2. Jansen B. J. M, Degroot A. Nat. Prod. Rep. 1991 8 319.
3. Vlad P. F, Koltsa M. N, Mironov G. N. Russ. Chem. Bull. 1997 46 855.
4. Spivey A. C, Weston M, Woodhead S. Chem. Soc. Rev. 2002 31 43.
5. Jansen B. J. M, de Groot A. Nat. Prod. Rep. 2004 21 449.
6. Urabe D, Inoue M. Tetrahedron 2009 65 6271.
7. Hog D. T, Webster R, Trauner D. Nat. Prod. Rep. 2012 29 752.
8. Jankowski P, Marczak S, Wicha J. Tetrahedron 1998 54 12071.
9. Hong B. C, Sarshar S. Org. Prep. Proced. Int. 1999 31 1.
10. Fleming F. F, Gudipati S. Eur. J. Org. Chem. 2008 5365.
11. Mander L. N. Chem. Rev. 1992 92 573.
12. Mander L. N. Nat. Prod. Rep. 2003 20 49.
13. Fujita E, Node M. Heterocycles 1977 7 709.
14. Mander L. N. Nat. Prod. Rep. 1988 5 541.
15. Wu Y, He Z. Highlights of Total Synthesis of Natural Products-Terpenes, Science Press, Beijing 2010 pp. 176-122 (in Chinese).
16. Gordon H. L, Freeman S, Hudlicky T. Synlett 2005 2911.
17. Tori M, Sono M, Asakawa Y. J. Chem. Soc. Perkin Trans. 1 1990 2849.
18. Tori M, Sono M, Nishigaki Y, Nakashima K, Asakawa Y. J. Chem. Soc. Perkin Trans. 1 1991 435.
19. Coates R. M, Sowerby R. L. J. Am. Chem. Soc. 1972 94 5386.
20. Piers E, Banville J. J. Chem. Soc. Chem. Commun. 1979 1138.
21. Piers E, Banville J, Lau C. K, Nagakura I. Can. J. Chem. 1982 60 2965.
22. Hughes R. C, Dvorak C. A, Meyers A. I. J. Org. Chem. 2001 66 5545.
23. Fukuzawa A, Sato H, Masamune T. Tetrahedron Lett. 1987 28 4303.
24. Sato Y, Mori M, Shibasaki M. Tetrahedron: Asymmetry 1995 6 757.
25. Piers E, Oballa R. M. J. Org. Chem. 1996 61 8439.
26. Piers E, Boulet S. L. Tetrahedron Lett. 1997 38 8815.
27. Huang X, Song L, Xu J, Zhu G, Liu B. Angew. Chem. Int. Ed. 2013 52 952.
28. Xie J, Ma Y, Horne D. A. J. Org. Chem. 2011 76 6169.
29. Nicolaou K. C, Snyder S. A, Montagnon T, Vassilikogiannakis G. Angew. Chem. Int. Ed. 2002 41 1668.
30. Takeda K, Sato M, Yoshii E. Tetrahedron Lett. 1986 27 3903.
31. Uenishi J, Kawahama R, Yonemitsu O. J. Org. Chem. 1997 62 1691.
32. Uenishi J, Kawahama R, Imakoga T, Yonemitsu O. Chem. Pharm. Bull. 1998 46 1090.
33. Hudlicky T, Radescakwart L, Li L. Q, Bryant T. Abstr. Pap. Am. Chem. Soc. 1988 196 64.
34. Hudlicky T, Radescakwart L, Li L. Q, Bryant T. Tetrahedron Lett. 1988 29 3283.
35. Hudlicky T, Fleming A, Radesca L. J. Am. Chem. Soc. 1989 111 6691.
36. Wender P. A, Singh S. K. Tetrahedron Lett. 1990 31 2517.
37. Attah-Poku S. K, Chau F, Yadav V. K, Fallis A. G. J. Org. Chem. 1985 50 3418.
38. Corey E. J, Desai M. C, Engler T. A. J. Am. Chem. Soc. 1985 107 4339.
39. Hog D. T, Mayer P, Trauner D. J. Org. Chem. 2012 77 5838.
40. Molander G. A, Quirmbach M. S, Silva L. F, Spencer K. C, Balsells J. Org. Lett. 2001 3 2257.
41. Qian S, Zhao G. Synlett 2011 722.
42. Qian S, Zhao G. Chem. Commun. 2012 48 3530.
43. Brady T. P, Kim S. H, Wen K, Theodorakis E. A. Angew. Chem. Int. Ed. 2004 43 739.
44. Brady T. P, Kim S. H, Wen K, Kim C, Theodorakis E. A. Chem.-Eur. J. 2005 11 7175.
45. Brady T. P, Guizzunti G, Kim S. H, Malhotra V, Theodorakis E. A. Abstr. Pap. Am. Chem. Soc. 2005 229 518.
46. Kende A. S, Chen J. J. Am. Chem. Soc. 1985 107 7184.
47. Loh T.-P, Hu Q.-Y. Org. Lett. 2000 3 279.
48. Niwa H, Mori T, Hasegawa T, Yamada K. J. Org. Chem. 1986 51 1015.
49. Niwa H, Nisiwaki M, Tsukada I, Ishigaki T, Ito S, Wakamatsu K, Mori T, Ikagawa M, Yamada K. J. Am. Chem. Soc. 1990 112 9001.
50. Ogura A, Yamada K, Yokoshima S, Fukuyama T. Org. Lett. 2012 14 1632.
51. Roberts R. A, Paquette L. A. Abstr. Pap. Am. Chem. Soc. 1983 185 179.
52. Paquette L. A, Wright J, Drtina G. J, Roberts R. A. J. Org. Chem. 1987 52 2960.
53. Wright J, Drtina G. J, Roberts R. A, Paquette L. A. J. Am. Chem. Soc. 1988 110 5806.
54. Ren L, Piers E. Tetrahedron Lett. 2012 53 3329.
55. Fürster A. Top. Catal. 1997 4 285.
56. Armstrong S. K. J. Chem. Soc. Perkin Trans. 1 1998 371.
57. Gradilla A, PÉrez-castells J. Angew. Chem. Int. Ed. 2006 45 6086.
58. Granger K, Snapper M. L. Eur. J. Org. Chem. 2012 2308.
59. Granger K. E, Casaubon R. L, Snapper M. L. Abs. Pap. Am. Chem. Soc. 2007 233.
60. Kim D, Kim I. H. Tetrahedron Lett. 1997 38 415.
61. Wang B, Tu Y.-Q. Acc. Chem. Res. 2011 44 1207.
62. Song Z-L, Fan C-A, Tu Y-Q. Chem. Rev 2011 11 7523.
63. Defaut B, Parsons T. B, Spencer N, Male L, Kariuki B. M, Grainger R. S. Org. Biomol. Chem. 2012 10 4926.
64. Prantz K, Mulzer J. Chem. Rev. 2010 110 3741.
65. Pati L. C, Roy A, Mukherjee D. Tetrahedron 2002 58 1773.
66. Brookhart M, Studabaler W. B. Chem. Rev. 1987 87 411.
67. Label H, Marcoux J.-F, Molinaro C, Charette A. B. Chem. Rev. 2003 103 977.
68. Fenlon T. W, Schwaebisch D, Mayweg A. V. W, Lee V, Adlington R. M, Baldwin J. E. Synlett 2007 2679.
69. Hodgson D. M, Chung Y. K, Paris J.-M. J. Am. Chem. Soc. 2004 126 8664.
70. Hodgson D. M, Chung Y. K, Paris J. M. Synthesis 2005 2264.
71. Hodgson D. M, Chung Y. K, Nuzzo I, Freixas G, Kulikiewicz K. K, Cleator E, Paris J.-M. J. Am. Chem. Soc. 2007 129 4456.
72. Hodgson D. M, Humphreys P. G, Miles S. M, Brierley C. A. J, War J. G. J. Org. Chem. 2007 72 10009.
73. Hodgson D. M, Salik S. Synlett 2009 1730.
74. Hodgson D. M, Salik S, Fox D. J. J. Org. Chem. 2010 75 2157.
75. Yue G, Yang L, Yuan C, Jiang X, Liu B. Org. Lett. 2011 13 5406.
76. Yue G, Yang L, Yuan C, Du B, Liu B. Tetrahedron 2012 68 9624.
77. Yue G, Yang L, Yuan C, Du B, Liu B. Chin. J. Org. Chem. 2013 33 90.
78. Yue G. Ph.D. Dissertation, Sichuan University, Chengdu, 2011 (in Chinese).
79. Cook S. P, Gaul C, Danishefsky S. J. Tetrahedron Lett. 2005 46 843.
80. Cook S. P, Polara A, Danishefsky S. J. J. Am. Chem. Soc. 2006 128 16440.
81. Tanaka T, Okuda O, Murakami K, Yoshino H, Mikamiyama H, Kanda A, Kim S. W, Iwata C. Chem. Pharm. Bull. 1995 43 1407.
82. Rahman S. M. A, Ohno H, Murata T, Yoshino H, Satoh N, Murakami K, Patra D, Iwata C, Maezaki N, Tanaka T. Org. Lett. 2001 3 619.
83. Rahman S. M. A, Ohno H, Murata T, Yoshino H, Satoh N, Murakami K, Patra D, Iwata C, Maezaki N, Tanaka T. J. Org. Chem. 2001 66 4831.