An oxidative dearomatization-induced [5 + 2] cascade enabling the syntheses of α-cedrene, α-pipitzol, and sec -cedrenol

Journal of the American Chemical Society

Volumn 133, Issue 5, 2011, Pages 1603-1608

  Green, Jason C ^a   Pettus, Thomas R R ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BENZYLIC; DEAROMATIZATION; EFFICIENT SYNTHESIS; ONE POT; SALICYL ALDEHYDE; STEREOCENTERS; TETHERED OLEFINS;

ACETIC ACID; BIOCHEMISTRY; OLEFINS;

PHENOLS;

ACETIC ACID; ALKENE; ALPHA CEDRENE; ALPHA PIPITZOL; CATION; CURCUPHENOL; HERBACEOUS AGENT; PHENOL DERIVATIVE; PHENOXONIUM; SALICYLALDEHYDE; SEC CEDRENOL; SESQUITERPENE DERIVATIVE; UNCLASSIFIED DRUG;

AROMATIZATION; ARTICLE; CHEMICAL MODIFICATION; CHEMICAL REACTION; CYCLOADDITION; DRUG STRUCTURE; DRUG SYNTHESIS; ENANTIOMER; RACEMIC MIXTURE;

OXIDATION-REDUCTION; OXYGEN; SESQUITERPENES;

EID: 79551696811     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja109925g     Document Type: Article

References (38)

1. Adams, R. P., McDaniel, C. A., and Carter, F. L. Biochem. Syst. Ecol. 1988, 16, 453-456
2. Clark, A. M., McChesney, J. D., and Adams, R. P. Phytother. Res. 1990, 4, 15-19
3. Oda, J., Ando, N., Nakajima, Y., and Inouye, Y. Agric. Biol. Chem. 1977, 41, 201-204
4. Walter, P. Annalen 1841, 39, 246
5. Walter, P. Annalen 1843, 48, 35-38
6. Stork, G. and Clarke, F. H. J. Am. Chem. Soc. 1955, 77, 1072-1073
7. Stork, G. and Clarke, F. H. J. Am. Chem. Soc. 1961, 83, 3114-3125
8. For a review of cedrene chemistry from 1955-2004: Hudlicky, T. and Reed, J. W. The Way of Synthesis; Wiley-VCH: Verlag GmbH & Co.: KGaA, Weinheim, 2007; pp 229 - 254.
9. Wender, P. A. and Howbert, J. J. J. Am. Chem. Soc. 1981, 103, 688-701
10. Walls, F., Padilla, P., Joseph-Nathan, P., Giral, F., and Romo, J. Tetrahedron Lett. 1965, 21, 1577-1582
11. Sanchez, I. H., Basurto, F., and Joseph-Nathan, P. J. Nat. Prod. 1984, 47, 382-383
12. Funk, R. L. and Bolton, G. L. J. Org. Chem. 1987, 52, 3174-3176
13. Pak, H., Canalda, I. I., and Fraser-Reid, B. J. Org. Chem. 1990, 55, 3009-3011
14. Takigawa, H., Kubota, H., Sonohara, H., Okuda, M., Tanaka, S., Fujikura, Y., and Ito, S. Appl. Environ. Mirocrob. 1993, 59, 1336-1341
15. Takigawa, H., Okuda, M., Etsuno, J., Fujikara, Y., and Ito, S. Jpn. Kokai Tokkyo Koho JP 06321884 A 19941122, 1994.
16. Takigawa, H., Okuda, M., Etsuno, J., and Fujikara, Y. Jpn. Kokai. Tokkyo Koho JP 06345642 A 19941220, 1994.
17. The following and references cited therein: Yamamura, S. and Nishiyama, S. Synlett 2002, 533-543
18. Quideau, S., Pouysegu, L., and Deffieux, D. Curr. Org. Chem. 2004, 8, 113-148
19. Buchi, G. and Chu, P. S. Tetrahedron 1981, 25, 4509-4513
20. Collins, J. L., Grieco, P. A., and Walker, J. K. Tetrahedron 1997, 26, 8975-8996
21. Engler, T. A. and Scheibe, C. M. J. Org. Chem. 1998, 63, 6247-6253
22. McEnroe, F. and Fenical, W. Tetrahedron 1978, 34, 1661-1664
23. Bohlmann, F. and Lonitz, M. Chem. Ber. 1978, 111, 843-852
24. Parker, W., Roberts, J. S., and Ramage, R. Q. Rev. (London) 1967, 21, 331-363
25. Van de Water, R. W., Magdziak, D. J., Chau, J. N., and Pettus, T. R. R. J. Am. Chem. Soc. 2000, 27, 6502-6503
26. Jones, R. M., Van de Water, R. W., Lindsey, C. C., and Pettus, T. R. R. J. Org. Chem. 2001, 10, 3435-3341
27. Selenski, C., Mejorado, L. H., and Pettus, T. R. R. Synlett 2004, 6, 1101-1103
28. Selenski, C. and Pettus, T. R. R. J. Org. Chem. 2004, 26, 9196-9203
29. Wessely, F. and Sinwel, F. Montash. Chem. 1950, 81, 1055-1070
30. Bowden, K., Heilbron, I. M., Jones, E. R. H., and Weedon, B. C. L. J. Chem. Soc. 1946, 39-45
31. Zhu, R., Xing, L., Wang, X., Cheng, C., Liu, B., and Hu, Y. Synlett 2007, 2267-2271
32. Furrow, M. E. and Myers, A. G. J. Am. Chem. Soc. 2004, 126, 5436-5445
33. 4 reduction of 38 (see the Supporting Information).
34. Barton, H. R. and McCombie, S. W. J. Chem. Soc., Perkin Trans. 1 1975, 1574-1585
35. Zhang, L. and Koreeda, M. J. Am. Chem. Soc. 2004, 126, 13190-13191
36. Radivoy, G., Alonso, F., Moglie, Y., Vitale, C., and Yus, M. Tetrahedron 2005, 61, 3859-3864 and references therein
37. Foley, D. A. and Maguire, A. R. Tetrahedron 2010, 66, 1131-1175
38. Sivik, M. R., Stanton, K. J., and Paquette, L. A. Org. Synth. 1998, 72, 57-61