Formal homoiodo allylsilane annulations: Dual total syntheses of (±)-hirsutene and (±)-capnellene

Journal of Organic Chemistry

Volumn 78, Issue 14, 2013, Pages 7112-7120

  Shen, Shou Jie ^a   Li, Wei Dong Z ^a,b  

^a LANZHOU UNIVERSITY   (China)

^b CHONGQING UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ALLYLSILANES; BI-FUNCTIONAL; CYCLOPENTENONES; SESQUITERPENES; SESQUITERPENOIDS; SYNTHONS; TOTAL SYNTHESIS; TRIQUINANE;

CHEMISTRY; ORGANIC COMPOUNDS;

SYNTHESIS (CHEMICAL);

[[3 (IODOMETHYL) 2 METHYL 5 (PROP 1 EN 2 YL)CYCLOHEX 1 EN 1 YL]METHYL]TRIMETHYLSILANE; [[3 (IODOMETHYL) 2 METHYLCYCLOPENT 1 EN 1 YL]METHYL]TRIMETHYLSILANE; [[3 (IODOMETHYL)CYCLOPENT 1 EN 1 YL]METHYL]TRIMETHYLSILANE; CAPNELLENE; CYCLOPENTENONE DERIVATIVE; HIRSUTENE; SESQUITERPENE DERIVATIVE; SILANE DERIVATIVE; UNCLASSIFIED DRUG;

ANNULATION REACTION; ARTICLE; CHEMICAL STRUCTURE; SYNTHESIS;

ALKENES; MOLECULAR STRUCTURE; SESQUITERPENES; SILANES; STEREOISOMERISM;

EID: 84880564501     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo4009854     Document Type: Article

References (82)

1. Mehta, G.; Srikrishna, A. Chem. Rev. 1997, 97, 671
2. Singh, V.; Thomas, B. Tetrahedron 1998, 54, 3647
3. Paquette, L. A. Curr. Org. Chem. 2002, 6, 1045
4. Little, R. D.; Muller, G. W. J. Am. Chem. Soc. 1981, 103, 2744
5. Little, R. D.; Carroll, G. L.; Petersen, J. L. J. Am. Chem. Soc. 1983, 105, 928
6. Curran, D. P.; Rakiewicz, D. M. J. Am. Chem. Soc. 1985, 107, 1448
7. Curran, D. P.; Chen, M.-H. Tetrahedron Lett. 1985, 26, 4991
8. Mehta, G.; Murthy, A. N.; Reddy, D. S. K.; Reddy, A. V. J. Am. Chem. Soc. 1986, 108, 3443
9. Iyoda, M.; Kushida, T.; Kitami, S.; Oda, M. J. Chem. Soc., Chem. Commun. 1986, 1049
10. Iyoda, M.; Kushida, T.; Kitami, S.; Oda, M. J. Chem. Soc., Chem. Commun. 1987, 1607
11. Anger, T.; Graalmann, O.; Schröder, H.; Gerke, R.; Kaiser, U.; Fitjer, L.; Noltemeyer, M. Tetrahedron 1998, 54, 10713
12. Leonard, J.; Bennett, L.; Mahmood, A. Tetrahedron Lett. 1999, 40, 3965
13. Banwell, M. G.; Edwards, A. J.; Harfoot, G. J.; Jolliffe, K. A. J. Chem. Soc., Perkin Trans. 1 2002, 2439
14. Singh, V.; Vedantham, P.; Sahu, P. K. Tetrahedron Lett. 2002, 43, 519
15. Wang, J.-C.; Krische, M. J. Angew. Chem., Int. Ed. 2003, 42, 5855
16. Lee, H.-Y.; Kim, Y. J. Am. Chem. Soc. 2003, 125, 10156
17. Banwell, M. G.; Edwards, A. J.; Harfoot, G. J.; Jolliffe, K. A. Tetrahedron 2004, 60, 535
18. Singh, V.; Vedantham, P.; Sahu, P. K. Tetrahedron 2004, 60, 8161
19. Jiao, L.; Yuan, C.; Yu, Z.-X. J. Am. Chem. Soc. 2008, 130, 4421
20. Chandler, C. L.; List, B. J. Am. Chem. Soc. 2008, 130, 6737
21. Fan, X.; Tang, M.-X.; Zhuo, L.-G.; Tu, Y. Q.; Yu, Z.-X. Tetrahedron Lett. 2009, 50, 155
22. Samajdar, S.; Patra, D.; Ghosh, S. Tetrahedron 1998, 54, 1789
23. Singh, V.; Prathap, S.; Porinchu, M. J. Org. Chem. 1998, 63, 4011
24. Liao, C.-C. Pure Appl. Chem. 2005, 77, 1221
25. Itano, W.; Ohshima, T.; Shibasaki, M. Synlett 2006, 3053
26. Lemière, G.; Gandon, V.; Cariou, K.; Hours, A.; Fukuyama, T.; Dhimane, A.-L.; Fensterbank, L.; Malacria, M. J. Am. Chem. Soc. 2009, 131, 2993
27. Nguyen, N. N. M.; Leclère, M.; Stogaitis, N.; Fallis, A. G. Org. Lett. 2010, 12, 1648
28. Hsu, D.-S.; Chou, Y.-Y.; Tung, Y.-S.; Liao, C.-C. Chem.-Eur. J. 2010, 16, 3121
29. Li, W.-D. Z.; Yang, J.-H. Org. Lett. 2004, 6, 1849
30. Corey, E. J.; Chaykovsky, M. J. Am. Chem. Soc. 1965, 87, 1353
31. Chandrasekhar, S.; Narasihmulu, C.; Jagadeshwar, V.; Reddy, K. V. Tetrahedron Lett. 2003, 44, 3629
32. Jiang, X.; Lim, Z.; Yeung, Y.-Y. Tetrehedron Lett. 2012, 54, 1798
33. Cohen, T.; McNamara, K.; Kuzemko, M. A.; Ramig, K.; Landi, J. J., Jr.; Dong, Y. Tetrahedron 1993, 49, 7931
34. Majetich, G.; Leigh, A. J.; Condon, S. Tetrahedron Lett. 1991, 32, 605
35. Kusuda, S.; Watanabe, Y.; Ueno, Y.; Toru, T. J. Org. Chem. 1992, 57, 3145
36. Geng, F.; Liu, J.; Paquette, L. A. Org. Lett. 2002, 4, 71
37. Hosomi, A.; Sakurai, H. Tetrahedron Lett. 1976, 17, 1295
38. Hosomi, A.; Sakurai, H. J. Am. Chem. Soc. 1977, 99, 1673
39. Wilson, S. R.; Price, M. F. J. Am. Chem. Soc. 1982, 104, 1124
40. Schinzer, D. Synthesis 1988, 263
41. Majetich, G.; Hull, K.; Defauw, J.; Shawe, T. Tetrahedron Lett. 1985, 26, 2755
42. Majetich, G.; Desmond, R. W., Jr.; Soria, J. J. J. Org. Chem. 1986, 51, 1753
43. Majetich, G.; Song, J. S.; Leigh, A. J.; Condon, S. M. J. Org. Chem. 1993, 58, 1030
44. Tori, M.; Makino, C.; Hisazumi, K.; Sono, M.; Nakashima, K. Tetrahedron: Asymmetry 2001, 12, 301
45. Shono, T.; Kise, N.; Fujimoto, T.; Tominaga, N.; Morita, H. J. Org. Chem. 1992, 57, 7175
46. Jung, M. E.; Rayle, H. L. J. Org. Chem. 1997, 62, 4601
47. Barton, D. H. R.; McCombie, S. W. J. Chem. Soc., Perkin Trans. 1 1975, 1574
48. Stork, G.; Danheiser, R. L. J. Org. Chem. 1973, 38, 1775
49. Majetich, G.; Song, J. S.; Ringold, C.; Nemeth, G. A.; Newton, M. G. J. Org. Chem. 1991, 56, 3973
50. Meister, P. G.; Sivik, M. R.; Paquette, L. A. Org. Synth. 1992, 70, 226
51. Meister, P. G.; Sivik, M. R.; Paquette, L. A.; Coffen, D. L. Org. Synth. 1998, 9, 570
52. Majetich, G.; Desmond, R.; Casares, A. M. Tetrahedron Lett. 1983, 24, 1913
53. Majetich, G.; Lowery, D.; Khetani, V.; Song, J. S.; Hull, K.; Ringold, C. J. Org. Chem. 1991, 56, 3988
54. Schinzer, D. Angew. Chem., Int. Ed. Engl. 1984, 23, 308
55. Tokoroyama, T.; Tsukamoto, M.; Iio, H. Tetrahedron Lett. 1984, 25, 5070
56. Schinzer, D.; Dettmer, G.; Ruppelt, M.; Sólyom, S.; Steffen, J. J. Org. Chem. 1988, 53, 3823
57. Majetich, G.; Defauw, J. Tetrahedron 1988, 44, 3833
58. Schuda, P. F.; Phillips, J. L.; Morgan, T. M. J. Org. Chem. 1986, 51, 2742
59. Kashima, H.; Kawashima, T.; Wakasugi, D.; Satoh, T. Tetrahedron 2007, 63, 3953
60. Sustmann, R.; Hopp, P.; Holl, P. Tetrahedron Lett. 1989, 30, 689
61. Sustmann, R.; Hopp, P.; Boese, R. J. Organomet. Chem. 1989, 375, 259
62. Manchand, P. S.; Yiannikouros, G. P.; Belica, P. S.; Madan, P. J. Org. Chem. 1995, 60, 6574
63. Van Arnum, S. D.; Moffet, H.; Carpenter, B. K. Org. Process Res. Dev. 2004, 8, 769
64. Sarkar, T. K.; Andersen, N. H. Tetrahedron Lett. 1978, 19, 3513
65. Denmark, S. E.; Weber, E. J. Helv. Chim. Acta 1983, 66, 1655
66. Denmark, S. E.; Weber, E. J. J. Am. Chem. Soc. 1984, 106, 7970
67. Denmark, S. E.; Almstead, N. G. J. Org. Chem. 1994, 59, 5130
68. Denmark, S. E.; Weber, E. J.; Almstead, N. G.; Wolf, L. M. Tetrahedron 2012, 68, 7701
69. Wu, Q.-X.; Shi, Y.-P.; Jia, Z.-J. Nat. Prod. Rep. 2006, 23, 699
70. Gao, J.-M.; Wu, W.-J.; Zhang, J.-W.; Konishi, Y. Nat. Prod. Rep. 2007, 24, 1153
71. Miller, D. J.; Allemann, R. K. Nat. Prod. Rep. 2012, 29, 60
72. Zhang, Z.; Li, W.-D. Z.; Li, Y.-L. Org. Lett. 2001, 3, 2555
73. Li, W.-D. Z.; Gao, Z.-H. Org. Lett. 2005, 7, 2917
74. Fleming, I. In Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I.; Paquette, L. A., Eds.; Pergamon Press: Oxford, U.K., 1991; Vol. 2, p 563.
75. Sarkar, T. K. In Science of Synthesis: Houben-Weyl Methods of Molecular Transformations; Fleming, I., Ed.; Georg Thieme Verlag: New York, 2002; Vol. 4, pp 837-962.
76. Masse, C. E.; Panek, J. S. Chem. Rev. 1995, 95, 1293
77. Langkopf, E.; Schinzer, D. Chem. Rev. 1995, 95, 1375
78. Fleming, I.; Barbero, A.; Walter, D. Chem. Rev. 1997, 97, 2063
79. Chabaud, L.; James, P.; Landais, Y. Eur. J. Org. Chem. 2004, 3173
80. Barbero, A.; Pulido, F. J. Acc. Chem. Res. 2004, 37, 817
81. Barbero, A.; García, C.; Pulido, F. J. Tetrahedron 2000, 56, 2739
82. Hanhan, N. V.; Ball-Jones, N. R.; Tran, N. T.; Franz, A. K. Angew. Chem., Int. Ed. 2012, 51, 989