First Synthesis of (+)-2,14-Deoxyalatol from α-Santonin

Chinese Journal of Chemistry

Volumn 22, Issue 4, 2004, Pages 377-383

  Xia, Wu Jiong ^a   Sun, Liang Dong ^a   Shi, Lei ^a   Zhang, Shu Yu ^a   Tu, Yong Qiang ^a  

^a LANZHOU UNIVERSITY   (China)

Author keywords

(+) 2,14 deoxyalatol; Dihydrofuran sesquiterpene; First synthesis

Indexed keywords

2,14 DEOXYALATOL; ACID; ALPHA SANTONIN; FURAN DERIVATIVE; SESQUITERPENE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL BOND; CYCLIZATION; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS;

EID: 2442457691     PISSN: 1001604X     EISSN: None     Source Type: Journal    
DOI: 10.1002/cjoc.20040220412     Document Type: Article

References (20)

1. Kuo, Y.-H.; King, M.-L.; Chen, C.-F.; Chen, H.-Y.; Chen, C.-H.; Chen, K. ; Lee, K.-H. J. Nat. Prod. 1994, 57, 263.
2. Takaishi, Y.; Ujita, K.; Tokuda, H.; Nishino, H.; Iwashima, A.; Fujita, T. Cancer Lett. 1992, 65, 19.
3. Zheng, Y. L.; Xu, Y.; Lin, J. F. Acta Pharm. Sin. 1989, 24, 568.
4. Wu, W. J.; Tu, Y. Q.; Liu, H. X.; Zhu, J. B. J. Nat. Prod. 1992, 55, 1294.
5. Duan, H.; Takaishi, Y.; Imakura, Y.; Jia, Y.; Li, T.; Cosentino, L. M.; Lee, K.-H. J. Nat. Prod. 2000, 63, 357.
6. White, J. D.; Shin, H.; Kim, T.-S.; Cutshall, N. S. J. Am. Chem. Soc. 1997, 119, 2404.
7. Tu, Y. Q.; Xia, W. J.; Shi, L. Chinese Patent No. 02108952.3, 2002.
8. Wu, D. G.; Liu, J. K.; Cheng, C. Q. Phytochemistry 1992, 31, 4219.
9. (a) Tu, Y. Q.; Hu, Y. J.; Wu, W. J.; Chen, N. Y.; Pan, X. F. Phytochemistry 1992, 31, 3633.
10. (b) Takaishi, Y.; Tokura, K.; Tamai, S.; Ujita, K.; Nakano, K.; Tomimatsu, T. Phytochemistry 1991, 30, 1567.
11. (c) Wu, D. G.; Liu, J. K.; Cheng, C. Q. Phytochemistry 1992, 31, 4219.
12. Xia, W. J.; Li, D. R.; Shi, L.; Tu, Y. Q. Tetrahedron Lett. 2002, 43, 627.
13. Rao, A. S.; Paknikar, S. M.; Kirtane, J. G. Tetrahedron 1983, 39, 2323.
14. Sun, L. D.; Tu, Y. Q.; Xia, W. J. Synth. Commun. 1998, 28, 3751.
15. Evans, D. A.; Dow, R. L.; Shin, T. L.; Takacs, J. M.; Zahler, R. J. Am. Chem. Soc. 1990, 112, 5290.
16. Srebnik, M.; Mechoulam, R. J. Chem. Soc., Chem. Commun. 1984, 1070.
17. Tu, Y. Q.; Sun, L. D. Tetrahedron Lett. 1998, 39, 7935.
18. Wu, W. J.; Tu, Y. Q.; Liu, H. X.; Zhu, J. B. J. Nat. Prod. 1992, 55, 1294.
19. Bates, H. A.; Fanina, J.; Tong, M. J. Org. Chem. 1986, 51, 2641.
20. Ando, M.; Akahane, A.; Takase, K. Bull. Chem. Soc. Jpn. 1978, 51, 284.