Synthesis of racemic Δ3-2-hydroxybakuchiol and its analogues

Helvetica Chimica Acta

Volumn 93, Issue 3, 2010, Pages 555-564

  Shi, Lei ^a,b   Lei, Xinsheng ^a   Zhang, Jiange ^b   Lin, Guoqiang ^a  

^a FUDAN UNIVERSITY   (China)

^b ZHENGZHOU UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENYL; ARYLATIONS; JOHNSON-CLAISEN REARRANGEMENTS; KEY FEATURE; NEGISHI CROSS-COUPLING; SYNTHETIC APPROACH;

ETHERS; PHENOLS;

SYNTHESIS (CHEMICAL);

6 ETHENYL 2,6 DIMETHYL 8 (4 METHYLPHENYL)OCTA 3,7 DIEN 2 OL; 6 ETHENYL 2,6 DIMETHYL 8 (NAPHTHALEN 2 YL)OCTA 3,7 DIEN 2 OL; 6 ETHENYL 2,6 DIMETHYL 8 [4 (TRIFLUOROMETHYL)PHENYL]OCTA 3,7 DIEN 2 OL; 6 ETHENYL 2,6 DIMETHYL 8 PHENYLOCTA 3,7 DIEN 2 OL; 6 ETHENYL 8 (4 METHOXYPHENYL) 2,6 DIMETHYLOCTA 3,7 DIEN 2 OL; 8 [4 [[(TERT BUTYL)DIPHENYLSILYL]OXY]PHENYL] 6 ETHENYL 2,6 DIMETHYLOCTA 3,7 DIEN 2 OL; ALKENYL GROUP; BAKUCHIOL; DELTA3 2 HYDROXYBAKUCHIOL; UNCLASSIFIED DRUG;

ARTICLE; ARYLATION; CHEMICAL REACTION; CROSS COUPLING REACTION; DRUG STRUCTURE; DRUG SYNTHESIS; PRIORITY JOURNAL; RACEMIC MIXTURE; REACTION ANALYSIS;

EID: 77949510034     PISSN: 0018019X     EISSN: 15222675     Source Type: Journal    
DOI: 10.1002/hlca.200900243     Document Type: Article

References (40)

1. 'Medicinal Plants in China', World Health Organization, Manila, 1986, p. 237.
2. J. A. Duke, E. S. Ayensu, 'Medicinal Plants of China', Reference Publications, Algonac Mich., 1985, Vol. 1, p. 338.
3. C.-Z. Wu, S. S. Hong, X. F. Cai, N. T. Dat, J.-X. Nan, B. Y. Hwang, J. J. Lee, D. Lee, Bioorg. Med. Chem. Lett. 2008, 18, 2619.
4. S. Yin, C.-Q. Fan, J.-M. Yue, J. Asian Nat. Prod. Res. 2007, 9, 29.
5. H. Matsuda, S. Sugimoto, T. Morikawa, K. Matsuhira, E. Mizuguchi, S. Nakamura, M. Yoshikawa, Chem. Pharm. Bull. 2007, 55, 106.
6. C.-Z. Wu, X. F. Cai, N. T. Dat, S. S. Hong, A.-R. Han, E.-K. Seo, B. Y. Hwang, J.-X. Nan, D. Lee, J. J. Lee, Tetrahedron Lett. 2007, 48, 8861.
7. S. Yin, C.-Q. Fan, L. Dong, J.-M. Yue, Tetrahedron 2006, 62, 2569.
8. C. N. Backhouse, C. L. Delporte, R. E. Negrete, S. Erazo, A. Zuñiga, A. Pinto, B. K. Cassels, J. Ethnopharmacol. 2001, 78, 27.
9. G. Mehta, U. R. Nayak, S. Dev, Tetrahedron Lett. 1966, 7, 4561.
10. G. Mehta, U. R. Nayak, S. Dev, Tetrahedron 1973, 29, 1119.
11. Y. H. Choi, G. H. Yon, K. S. Hong, D. S. Yoo, C. W. Choi, W.-K. Park, J. Y. Kong, Y. S. Kim, S. Y. Ryu, Planta Med. 2008, 74, 1405.
12. Y.-C. Kim, H. Oh, B. S. Kim, T.-H. Kang, E.-K. Ko, Y. M. Han, B. Y. Kim, J. S. Ahn, Planta Med. 2005, 71, 87.
13. E.-J. Park, Y.-Z. Zhao, Y.-C. Kim, D. H. Sohn, Eur. J. Pharmacol. 2007, 559, 115.
14. S. Adhikari, R. Joshi, B. S. Patro, T. K. Ghanty, G. J. Chintalwar, A. Sharma, S. Chattopadhyay, T. Mukherjee, Chem. Res. Toxicol. 2003, 16, 1062.
15. H. Haraguchi, J. Inoue, Y. Tamura, K. Mizutani, Phytother. Res. 2002, 16, 539.
16. H. Cho, J.-Y. Jun, E.-K. Song, K.-H. Kang, H.-Y. Baek, Y.-S. Ko, Y.-C. Kim, Planta Med. 2001, 67, 750.
17. H. Haraguchi, J. Inoue, Y. Tamura, K. Mizutani, Planta Med. 2000, 66, 569.
18. J. M. Krenisky, J. Luo, M. J. Reed, J. R. Carney, Biol. Pharm. Bull. 1999, 22, 1137.
19. N. J. Sun, S. H. Woo, J. M. Cassady, R. M. Snapka, J. Nat. Prod. 1998, 61, 362.
20. T. Esumi, H. Shimizu, A. Kashiyama, C. Sasaki, M. Toyota, Y. Fukuyama, Tetrahedron Lett. 2008, 49, 6846.
21. X.-L. Du, H.-L. Chen, H.-J. Feng, Y.-C. Li, Helv. Chim. Acta 2008, 91, 371.
22. H. Chen, Y. Li, Lett. Org. Chem. 2008, 5, 467.
23. J. Fujiwara, M. Watanabe, T. Sato, J. Chem. Soc., Chem. Commun. 1994, 349.
24. S. Araki, Y. Bustugan, J. Chem. Soc., Perkin Trans. 1 1991, 2395.
25. J. Crabduff, J. A. Miller, J. Chem. Soc. C 1968, 2671.
26. J. Crabduff, J. A. Miller, Chem. Commun. 1967, 606.
27. C. Labbé, F. Faini, J. Coll, J. D. Connolly, Phytochemistry 1996, 42, 1299.
28. C. C. Shah, V. K. Bhalla, S. Dev, J. Indian Chem. Soc. 1997, 74, 970.
29. G. Zhao, S.-Y. Zang, X.-W. Zheng, X.-H. Zhang, L.-H. Guo, Biochem. Pharmacol. 2008, 75, 1835.
30. H. Chen, X. Du, W. Tang, Y. Zhou, J. Zuo, H. Feng, Y. Li, Bioorg. Med. Chem. 2008, 16, 2403.
31. H. Miyaoka, Y. Isaji, Y. Kajiwara, I. Kunimune, Y. Yamada, Tetrahedron Lett. 1998, 39, 6503.
32. C. Xia, L. Heng, D. Ma, Tetrahedron Lett. 2002, 43, 9405.
33. A. Eisenführ, P. S. Arora, G. Sengle, L. R. Takaoka, J. S. Nowick, M. Famulok, Bioorg. Med. Chem. 2003, 11, 235.
34. J. Christoffers, A. Baro, Angew. Chem., Int. Ed. 2003, 42, 1688.
35. F. E. Ziegler, Chem. Rev. 1988, 88, 1423.
36. S. Blechert, Synthesis 1989, 71.
37. K. Takai, K. Nitta, K. Utimoto, J. Am. Chem. Soc. 1986, 108, 7408.
38. T. Okazoe, K. Takai, K. Utimoto, J. Am. Chem. Soc. 1987, 109, 951.
39. J. Augé, V. Boucard, R. Gil, N. Lubin-Germain, J. Picard, J. Uziel, Synth. Commun. 2003, 33, 3733.
40. A. C. Spivey, T. Fekner, S. E. Spey, H. Adams, J. Org. Chem. 1999, 64, 9430.