Synthesis of (+/-)-curcumene ether

Synlett

Volumn , Issue 9 SPEC. ISS., 2003, Pages 1349-1351

  Vickers, Troy D ^a   Keay, Brian A ^a  

^a UNIVERSITY OF CALGARY   (Canada)

Author keywords

Intramolecular Heck reaction; Lactones; Natural products; Spiro compounds; Total synthesis

Indexed keywords

2 AMINO 5 METHYLPHENOL; 5 BROMO 2 METHYL 2 PENTENE; BROMINE DERIVATIVE; CURCUMENE ETHER; ETHER DERIVATIVE; PHENOL DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; HECK REACTION; NONHUMAN; STEREOCHEMISTRY; SYNTHESIS;

EID: 0038780097     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2003-40343     Document Type: Article

References (32)

1. (a) Maddaford, S. P.; Andersen, N. G.; Cristofoli, W. A.; Keay, B. A. J. Am. Chem. Soc. 1996, 118, 10766.
2. (b) Lau, S. Y. W.; Keay, B. A. Org. Lett. 2001, 3, 181.
3. (c) Lau, S. Y. W.; Keay, B. A. Synlett 1999, 605.
4. (d) Keay, B. A.; Maddaford, S. P.; Cristofoli, W. A.; Andersen, N. G.; Passafaro, M. S.; Wilson, N. S.; Nieman, J. A. Can. J. Chem. 1996, 75, 1163.
5. (e) Cristofoli, W. A.; Keay, B. A. Synlett 1994, 625.
6. Woo, S.; Keay, B. A. Synlett 1996, 135.
7. (a) Poli, G.; Giambastiani, G.; Heumann, A. Tetrahedron 2000, 56, 5959.
8. (b) Ikeda, M.; ElBialy, S. A. A.; Yakura, T. Heterocycles 1999, 51, 1957.
9. (c) Link, J. T.; Overman, L. E. In Metal-Catalyzed Cross-Coupling Reactions; Diederich, F.; Stang, P. J., Eds.; Wiley-VCH, Inc.: New York NY, 1998, 231.
10. (d) Shibasaki, M.; Boden, C. D. J.; Kojima, A. Tetrahedron 1997, 53, 7371.
11. (e) Gibson, S. E.; Middleton, R. J. Contemp. Org. Synth. 1996, 3, 447.
12. (a) Tomida, B.; Hirose, Y.; Nakatsuka, T. Mokuaai Gakkaishi 1969, 15, 47.
13. (b) Tomida, B.; Hirose, Y. Mokuzai Gakkaishi 1969, 15, 337.
14. Vig, O. P.; Kumar, H.; Salota, J. P.; Sharma, S. D. Indian J. Chem. 1973, 11, 86.
15. Paknikar, S. K.; Dinge, A. S. Indian J. Chem. 1980, 19, 80.
16. Mashrequi, S. H.; Trivedi, G. K. Indian J. Chem. 1978, 16, 849.
17. Kametani, T.; Kawamura, K.; Tsubuki, M.; Honda, T. J. Chem. Soc., Perkin Trans. 1 1984, 1305.
18. Serra, S. Synlett 2000, 890.
19. Purchased from the Aldrich Chemical Company.
20. (a) Sawaguchi, M.; Fukuhara, T.; Yoneda, N. J. Fluor. Chem. 1999, 97, 127.
21. (b) Yoneda, N.; Fukuhara, T.; Mizokami, T.; Suzuki, A. Chem. Lett. 1991, 459.
22. Cambie, R. C.; Rutledge, P. S.; Smith-Palmer, T.; Woodgate, P. D. J. Chem. Soc., Perkin Trans. 1 1976, 1161.
23. Hiranuma, S.; Shibata, M.; Hudlicky, T. J. Org. Chem. 1983, 48, 5321.
24. (a) Ashimori, A.; Bachand, B.; Overman, L. E.; Poon, D. J. J. Am. Chem. Soc. 1998, 120, 6477.
25. (b) Ashimori, A.; Bachand, B.; Calter, M. A.; Govek, S. P.; Overman, L. E.; Poon, D. J. J. Am. Chem. Soc. 1998, 120, 6488.
26. +): 244.10994, found: 244.10954.
27. 20 gave racemic mixtures of double bond isomers 12 and 13.
28. (a) Fuganti, C.; Serra, S. J. Org. Chem. 1999, 64, 8728.
29. (b) Rossi, R. A.; Bunnett, J. F. J. Org. Chem. 1973, 38, 2314.
30. Andersen, N. G.; Parvez, M.; Keay, B. A. Org. Lett. 2000, 2, 2817.
31. Andersen, N. G.; McDonald, R.; Keay, B. A. Tetrahedron: Asymmetry 2001, 12, 263.
32. Loiseleur, O.; Hayashi, M.; Schmees, N.; Pfaltz, A. Synthesis 1997, 1338.