Aliphatic C-H to C-C conversion: Synthesis of (-)-cameroonan-7α-ol

Journal of Organic Chemistry

Volumn 76, Issue 6, 2011, Pages 1874-1882

  Taber, Douglass F ^a   Nelson, Christopher G ^a  

^a UNIVERSITY OF DELAWARE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

C-C BONDS; C-H BOND; SESQUITERPENES; STEREOGENIC CENTERS;

ALIPHATIC COMPOUND; CAMEROONAN 7ALPHA OL; CARBON; CITRONELLAL; HYDROGEN; SESQUITERPENE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL BOND; HYDROGEN BOND; SYNTHESIS;

CARBON; CATALYSIS; CYCLIZATION; HYDROGEN; MANGANESE; OXIDATION-REDUCTION; RHODIUM; SESQUITERPENES; STEREOISOMERISM;

EID: 79953836126     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo200075v     Document Type: Article

References (57)

1. Weyerstahl, P.; Marschall, H.; Seelmann, I.; Jakupovic, J. Eur. J. Org. Chem. 1998, 1205.
2. (a) Coates, R. M.; Ho, Z.; Klobus, M.; Wilson, S. R. J. Am. Chem. Soc. 1996, 118, 9249.
3. (b) Coates, R. M.; Ho, J. Z.; Klobus, M.; Zhu, L. J. Org. Chem. 1998, 63, 9166.
4. (c) Bohlmann, F.; Jakupovic, J. Phytochemistry 1980, 19, 259.
5. (d) Fitjer, L.; MonzóOhra, H. J. Org. Chem. 1993, 58, 6171.
6. (a) Davis, C. E.; Duffy, B. C.; Coates, R. M. Org. Lett. 2000, 2, 2717.
7. (b) Davis, C. E.; Duffy, B. C.; Coates, R. M. J. Org. Chem. 2003, 68, 6935.
8. (c) Schmidt, A. W.; Olpp, T.; Schmid, S.; Goutal, S.; Jäger, A.; Knölker, H.-J. Synlett 2007, 2007, 1549.
9. (d) Schmidt, A. W.; Olpp, T.; Schmid, S.; Jäger, A.; Knölker, H.-J. Tetrahedron 2009, 65, 5484.
10. For recent examples of intramolecular aliphatic C-H to C-O conversion, see: (a) Stang, E.; White, M. C. Nat. Chem. 2009, 1, 547.
11. (b) Kasuya, S.; Kamijo, S.; Inoue, M. Org. Lett. 2009, 11, 3630.
12. For recent examples of intermolecular aliphatic C-H to C-O conversion, see: (c) Chen, M. S.; White, M. C. Science 2007, 318, 783.
13. (d) Chen, K.; Baran, P. S. Nature 2009, 459, 824.
14. (e) Gomez, L.; Garcia-Bosch, I.; Company, A.; Benet-Buchholz, J.; Polo, A.; Sala, X.; Ribas, X.; Costas, M. Angew. Chem., Int. Ed. 2009, 48, 5720.
15. (f) Ishihara, Y.; Baran, P. S. Synlett 2010, 1733.
16. For a general overview of recents advances in C-H functionalization, see: (g) Lyons, T.; Sanford, M. S. Chem. Rev. 2010, 110, 1147 and the other articles in that themed issue.
17. For recent examples of intramolecular aliphatic C-H to C-C bond formation, see: (a) Wolckenhauer, S. A.; Devlin, A. S.; DuBois, J. Org. Lett. 2007, 9, 4363.
18. (b) Herrera, A. J.; Rondon, M.; Suárez, E. J. Org. Chem. 2008, 73, 3384.
19. (c) Taber, D. F.; Tian, W. J. Org. Chem. 2008, 73, 7560.
20. (d) Bequette, J. P.; Jungong, C. S.; Novikov, A. V. Tetrahedron Lett. 2009, 50, 6963.
21. (e) McQuaid, K. M.; Sames, D. J. Am. Chem. Soc. 2009, 131, 402.
22. (f) Wasa, M.; Engle, K. M.; Yu, J.-Q. J. Am. Chem. Soc. 2009, 131, 9886.
23. For recent examples of intermolecular aliphatic C-H to C-C bond formation, see: (g) Yoshimitsu, T.; Matsuda, K.; Nagaoka, K.; Tanaka, T. Org. Lett. 2007, 9, 5115.
24. (h) Matsuo, J.; Tanaki, Y.; Ishibashi, H. Tetrahedron Lett. 2007, 18, 3233.
25. (i) Wang, D.-H.; Wasa, M.; Giri, R.; Yu, J.-Q. J. Am. Chem. Soc. 2008, 130, 7190.
26. (j) Nadeau, E.; Li, Z.; Morton, D.; Davies, H. M. L. Synlett 2009, 151.
27. (k) Protti, S.; Ravelli, D.; Fagnoni, M.; Albini, A. Chem. Commun. 2009, 7351.
28. For a review of C-H to C-C bond functionalization, see: (l) Taber, D. F.; Stiriba, S.-E. Natural Product Synthesis by Rh-Mediated Intramolecular C-H Insertion. In Organic Synthesis Highlights IV; Schmalz, H.-G., Ed.; Wiley-VCH Verlag GmbH: Weinheim, Germany, 2008.
29. For the first uses of RhII-mediatedC-HtoC-Cbond formation in naturalproduct synthesis, see: (a)Taber, D. F.;Schuchardt, J. S. J. Am. Chem. Soc. 1985, 107, 3618.
30. (b) Taber, D. F.; Raman, K.; Gaul, M. D. J. Org. Chem. 1987, 52, 28.
31. For more recent examples see: (c) Taber, D. F.; Frankowski, K. J. J. Org. Chem. 2005, 70, 6417.
32. (d) Reference 5c. For a review
33. see: (e) Taber, D. F.; Stiriba, S.-E. Chem.-Eur. J. 1998, 4, 990.
34. Taber, D. F.; Petty, E. H. J. Am. Chem. Soc. 1985, 107, 196.
35. Overberger, C. G.; Ozaki, S.; Braunstein, D. M. Makromol. Chem. 1966, 93, 13.
36. Pospíšil, J.; Markó, I. E. J. Am. Chem. Soc. 2007, 129, 3516.
37. Hannick, S. M.; Kishi, Y. J. Org. Chem. 1983, 48, 3833.
38. (a) Shin, H.; Choi, B. S.; Lee, K. K.; Choi, H.-W.; Chang, J. H.; Lee, K. W.; Nam, D. H.; Kim, N.-S. Synthesis 2004, 2004, 2629.
39. Taber, D. F.; Ruckle, R. E., Jr.; Hennessy, M. J. J. Org. Chem. 1986, 51, 4077.
40. (a) Kates, S. A.; Dombroski, M. A.; Snider, B. B. J. Org. Chem. 1990, 55, 2427.
41. (b) Snider, B. B.; Merritt, J. E.; Dombroski, M. A.; Buckman, B. O. J. Org. Chem. 1991, 56, 5544.
42. (a) Beckwith, A. L. J.; Phillipou, B. G. J. Am. Chem. Soc. 1974, 96, 1613.
43. (b) Schwartz, C. E.; Curran, D. P. J. Am. Chem. Soc. 1990, 112, 9272.
44. (c) Taber, D. F.; Wang, Y.; Stachel, S. J. Tetrahedron Lett. 1993, 34, 6209.
45. See Supporting Information for analysis of this complex mixture.
46. (a) Taber, D. F.; Nelson, C. G. J. Org. Chem. 2006, 71, 8973.
47. (b) Huang, H.; Nelson, C. G.; Taber, D.F. Tetrahedron Lett. 2010, 51, 3545.
48. (a) Poon, K. W. C.; House, S. E.; Dudley, G. B. Synlett 2005, 3142.
49. (b) Poon, K. W. C.; Dudley, G. B. J. Org. Chem. 2006, 71, 3923.
50. Banerjee, S.; Das, J.; Santra, S. Tetrahedron Let. 2009, 50, 124.
51. (a) Bickart, P.; Carson, F. W.; Jacobus, J.; Miller, E. G.; Mislow, K. J. Am. Chem. Soc. 1968, 90, 4869.
52. (b) Pelc, M. J.; Zakarian, A. Tetrahedron Lett. 2006, 47, 7519.
53. Marcantoni, E.; Cingolani, S. J. Org. Chem. 1998, 63, 3624.
54. Banerjee, A. K.; Matheud, C. A. P.; Hurtado, S.; Diaz, M. G. Heterocycles 1986, 24, 2155.
55. Girard, P.; Namy, J. L.; Kagan, H. B. J. Am. Chem. Soc. 1980, 102, 2693.
56. Micovic, V. M.; Mihailovic, M. L. J. J. Org. Chem. 1953, 18, 1190.
57. 13C multiplicities were determined with the aid of a JVERT pulse sequence, differentiating the signals for methyl and methane carbons as "d" and for methylene and quaternary carbons as "u".