Efficient asymmetric synthesis of chiral monomer of epoxyquinols and (-)-phyllostine

Bulletin of the Korean Chemical Society

Volumn 31, Issue 4, 2010, Pages 1047-1050

  Chae, Hee Il ^a   Hwang, Geum Sook ^b   Jin, Ming Yu ^a   Ryu, Do Hyun ^a  

^a Sungkyunkwan University   (South Korea)

^b Chungnam National University   (South Korea)

Author keywords

Angiogenesis; Asymmetric catalyst; Diels alder reaction; Epoxidation; Epoxyquinol

Indexed keywords

EID: 77951941968     PISSN: 02532964     EISSN: 12295949     Source Type: Journal    
DOI: 10.5012/bkcs.2010.31.04.1047     Document Type: Article

References (38)

1. Carmeliet, P. Angiogenesis in Health and Disease; Nat. Med. 2003, 9, 653.
2. Soker, S.; Takashima, S.; Miao, H. Q.; Neufeld, G.; Klagsbrun, M. Cell 1998, 92, 735.
3. Kerbel, R. S. Bioessays 1991, 13, 31.
4. Gasparini, G. Drugs 1999, 58, 17.
5. Ryan, C. J.; Wilding, G. Drugs & Aging 2000, 17, 249.
6. (a) Hiroshi, K.; Onose, R.; Koshino, H.; Yoshida, A.; Kobayashi, K.; Kageyama, S.-I.; Osada, H. J. Am. Chem. Soc. 2002, 124, 3496.
7. (b) Kakeya, H.; Onose, R.; Yoshida, A.; Koshino, H.; Osada, H. J. Antibiot. 2002, 55, 829.
8. (a) Kamiyama, H.; Hideaki, K.; Takeo, U.; Kiyohiro, N.; Mitsuru, S.; Yujiro, H.; Hiroyuki, O. Oncology Research 2008, 17, 11.
9. (b) Kamiyama, H.; Usui, T.; Uramoto, M.; Takagi, H.; Shoji, M.; Hayashi, Y.; Kakeya, H.; Osada, H. J. Antibiot. 2008, 61, 94.
10. (c) Kamiyama, H.; Usui, T.; Sakurai, H.; Shoji, M.; Hayashi, Y.; Kakeya, H.; Osada, H. Biosci. Biotechnol. Biochem. 2008, 72, 1894.
11. (a) Shoji, M.; Yamaguchi, J.; Kakeya, H.; Osada, H.; Hayashi, Y. Angew. Chem. Int. Ed. 2002, 41, 3192.
12. (b) Shoji, M.; Imai, H.; Mukaida, M.; Sakai, K.; Kakeya, H.; Osada, H.; Hayashi, Y. J. Org. Chem. 2005, 70, 79.
13. (c) Li, C.; Bardhan, S.; Pace, E. A.; Liang, M.-C.; Gilmore, T. D.; Porco. J. A., Jr. Org. Lett. 2002, 4, 3267.
14. (d) Mehta, G.; Islam, K. Tetrahedron Lett. 2004, 45, 3611.
15. (e) Kuwahara, S.; Imada, S. Tetrahedron Lett. 2005, 46, 547.
16. (a) Sakamura, S.; Ito, J.; Sakai, R. Agr. Biol. Chem. 1970, 34, 153.
17. (b) Sakamura, S.; Ito, J.; Sakai, R. Agr. Biol. Chem. 1971, 35, 105.
18. (c) Ichihara, A.; Oda, K.; Sakamura, S.; Tetrahedron Lett. 1972, 50, 5105.
19. (d) Ichihara, A.; Kimura, R.; Oda, K.; Sakamura, S. Tetrahedron Lett. 1976, 51, 4741.
20. (e) Okamura, H.; Shimizu, H.; Yamashita, N.; Iwagawa, T.; Nakatani, M. Tetrahedron 2003, 59, 10159.
21. (f) Mehta, G.; Islam, K. Tetrahedron Lett. 2004, 45, 7683.
22. (g) Yoshida, N.; Konno, H.; Kamikubo, T.; Takahashi, M.; Ogasawara, K. Tetrahedron 1999, 10, 3849.
23. Bayón, P.; Marjanet, G.; Toribio, G.; Alibés, R.; March, P. D.; Figueredo, M.; Font, J. J. Org. Chem. 2008, 73, 3486.
24. (a) The Mikami catalyst has also been found to afford good results with 1,4-quinone monoketals as substrates. see: Breuning, M.; Corey, E. J. Org. Lett. 2001, 3, 1559.
25. (b) Ryu, D. H.; Zhou, G.; Corey, E. J. J. Am. Chem. Soc. 2004, 126, 4800.
26. (c) Ryu, D. H.; Corey, E. J. J. Am. Chem. Soc. 2003, 125, 6388.
27. (d) Ryu, D. H.; Lee, T. W. Corey, E. J. J. Am. Chem. Soc. 2002, 124, 9992.
28. (e) Ryu, D. H.; Kim, K. H.; Sim, J. Y.; Corey, E. J. Tetrahedron Lett. 2007, 48, 5735.
29. (f) Lee, M. Y.; Kim, K. H.; Jiang, S.; Jung, Y. H.; Sim, J. Y.; Hwang, G.-S.; Ryu, D. H. Tetrahedron Lett. 2008, 49, 1965.
30. (g) Sim, J. Y.; Hwang, G.-S.; Kim, K. H.; Ko, E. M.; Ryu, D. H. Chem. Commun. 2007, 5064.
31. (h) Corey, E. J. Angew. Chem. Int. Ed. 2009, 48, 2100.
32. (i) Senapati, B. K.; Hwang, G.-S.; Lee, S.; Ryu, D. H. Angew. Chem. Int. Ed. 2009, 48, 4398.
33. (j) Gao, L.; Hwang, G.-S.; Lee, M. Y.; Ryu, D. H. Chem. Commun. 2009, 5460.
34. (k) Kim, J. Y.; Hwang, G.-S.; Lee, S. M.; Han, J. H.; Kim, E. Y.; Ryu, D. H. Bull. Korean Chem. Soc. 2009, 30, 289.
35. (l) Jin, M. Y.; Hwang, G.-S.; Chae, H. I.; Jung, S. H.; Ryu, D. H. Bull. Korean Chem. Soc. 2010, 31, 727.
36. Triflic acid activated catalyst 6 provided the Diels-Alder adduct 9 with better enantioselectivity compared to triflimide or aluminium bromide activated catalyst.
37. 2. Crystallographic data for the structure reported here have been deposited with the Cambridge Crystallographic Data Centre (Deposition No. CCDC-763142). That data can be obtained free of charge via http://www.ccdc.camac.uk/perl/catreq.cgi (or from the CCDC, 12 Union Road, Cambridge CB2 1EZ, UK; fax: +44 1223 336033; e-mail: deposit@ccdc.cam.ac. uk).
38. Kiyooka, S.-I.; Kuroda, H.; Shimasaki, Y. Tetrahedron Lett. 1986, 27 3009.