Stereocontrolled synthesis of enantiopure anticancer cyclopentenone prostaglandin analogues: (-)- and (+)-TEI-9826

Tetrahedron Asymmetry

Volumn 21, Issue 23, 2010, Pages 2794-2799

  Urawiński, Remigiusz ^a   Mikina, MacIej ^a   Mikołajczyk, Marian ^a  

^a CENTRE OF MOLECULAR AND MACROMOLECULAR STUDIES   (Poland)

Author keywords

[No Author keywords available]

Indexed keywords

CAMPHOR; CARBON; CYCLOPENTENONE; PROSTAGLANDIN DERIVATIVE; TEI 9826; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; ARTICLE; CHIRALITY; ENANTIOMER; HYDROGENATION; PRIORITY JOURNAL; STEREOCHEMISTRY; SYNTHESIS;

EID: 78651380160     PISSN: 09574166     EISSN: 1362511X     Source Type: Journal    
DOI: 10.1016/j.tetasy.2010.11.007     Document Type: Article

References (24)

1. For a review on biological properties of cyclopentenone PGs, see: D.S. Strauss, and C.K. Glass Med. Res. Rev. 21 2001 185 210
2. S. Fukushima, Y. Takeuchi, S. Kishimoto, S. Yamashita, K. Uetsuki, S. Shirakawa, M. Suzuki, K. Furata, R. Noyori, H. Sasaki, Y. Kikuchi, T. Kita, T. Yamori, J. Sawada, M. Kojima, A. Hazato, S. Kurozumi, and M. Fukushima Anti-Cancer Drugs 12 2001 221 234
3. H. Sasaki, S. Niimi, M. Akiyama, T. Tanaka, S. Kurozumi, and M. Fukushima Cancer Res. 59 1999 3919 3922
4. S. Fukushima, S. Kishimoto, Y. Takeuchi, and M. Fukushima Adv. Drug Delivery Rev. 45 2000 65 75
5. K. Furuta, K. Tomokiyo, T. Satoh, Y. Watanabe, and M. Suzuki ChemBioChem 1 2000 283 286
6. K. Furuta, M. Maeda, Y. Hirata, S. Shibata, K. Kiuchi, and M. Suzuki Bioorg. Med. Chem. Lett. 17 2007 5487 5491
7. For a recent review on the synthesis of prostaglandins and analogues, see: S. Das, S. Chandrasekhar, J. Singh Yadar, and R. Grée Chem. Rev. 107 2007 3286 3337
8. S. Sugiura, T. Toru, T. Tanaka, A. Hazato, N. Okamura, K. Bannai, K. Manabe, S. Kurozumi, and R. Noyori Chem. Pharm. Bull. 32 1984 4658 4661
9. S. Sugiura, A. Hazato, T. Tanaka, K. Okamura, K. Bannai, S. Manabe, S. Kurozumi, and R. Noyori Chem. Pharm. Bull. 33 1985 4120 4133
10. M. Suzuki, Y. Morita, H. Koyano, M. Koga, and R. Noyori Tetrahedron 46 1990 4809 4822
11. M. Iqbal, and P. Evans Tetrahedron Lett. 44 2003 5741 5745
12. R. Weaving, E. Roulland, C. Monneret, and J.-C. Florent Tetrahedron Lett. 44 2003 2579 2581
13. M. Schelwies, P. Dübon, and G. Helmchen Angew. Chem., Int. Ed. 45 2006 2466 2469
14. P. Dübon, M. Schelwies, and G. Helmchen Chem. Eur. J. 14 2008 6722 6733
15. M. Mikołajczyk Rev. Heteroat. Chem. 2 1993 19 39
16. M. Mikołajczyk, and P. Bałczewski Top. Curr. Chem. 223 2002 161 214
17. M. Mikołajczyk, M. Mikina, M. Wieczorek, and J. Błaszczyk Angew. Chem., Int. Ed. 35 1996 1560 1562
18. Mikina, M.; Mikołajczyk, M.; Jankowiak, A. Patent PL 336, 531, 2004.
19. C.M.D. Beels, M.J. Coleman, and R.J.K. Taylor Synlett 1990 479 480
20. D.O. Jang, and Y.H. Joo Synlett 1997 279 280
21. D.O. Jang, and Y.H. Joo Synth. Commun. 28 1998 871 877 and references cited therein
22. C.R. Johnson, and T.D. Penning J. Am. Chem. Soc. 117 1988 4726 4735
23. Y. Kobayashi, M.G. Murugesh, M. Nakano, E. Takahisa, S.B. Usmani, and T. Ainai J. Org. Chem. 67 2002 7110 7123
24. For a short discussion on the steric course of the aldol reaction at the α′-position of cyclopentenone see: Y. Kobayashi, M.G. Murugesh, and M. Nakano Tetrahedron Lett. 42 2001 1703 1707