Studies toward the synthesis of luminacin D: Assembly of simplified analogues devoid of the epoxide displaying antiangiogenic activity

Organic Letters

Volumn 6, Issue 22, 2004, Pages 3909-3912

  Davies, Mark W ^a   Maskell, Lesley ^b   Shipman, Michael ^a   Slawin, Alexandra M Z ^c   Vidot, Sandrine M E ^a   Whatmore, Jacqueline L ^b  

^a UNIVERSITY OF WARWICK   (United Kingdom)

^b PENINSULA MEDICAL SCHOOL   (United Kingdom)

^c UNIVERSITY OF ST ANDREWS   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ANGIOGENESIS INHIBITOR; LUMINACIN D; UNCLASSIFIED DRUG;

ALDOL REACTION; ANTIANGIOGENIC ACTIVITY; ARTICLE; CONTROLLED STUDY; DRUG ACTIVITY; DRUG SYNTHESIS; HUMAN; HUMAN CELL; STEREOCHEMISTRY;

EID: 8744312668     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol048462v     Document Type: Article

References (23)

1. Carmeliet, P.; Jain, R. K. Nature 2000, 407, 249.
2. King, R. J. B. Cancer Biology; Longman: Edinburgh, 1996.
3. Han, Z. C.; Liu, Y. Int. J. Hematol. 1999, 70, 68. Eatock, M. M.; Schätzlein, A.; Kaye, S. B. Cancer Treat. Rev. 2000, 26, 191. Matter, A. Drug Discovery Today 2001, 6, 1005.
4. Han, Z. C.; Liu, Y. Int. J. Hematol. 1999, 70, 68. Eatock, M. M.; Schätzlein, A.; Kaye, S. B. Cancer Treat. Rev. 2000, 26, 191. Matter, A. Drug Discovery Today 2001, 6, 1005.
5. Han, Z. C.; Liu, Y. Int. J. Hematol. 1999, 70, 68. Eatock, M. M.; Schätzlein, A.; Kaye, S. B. Cancer Treat. Rev. 2000, 26, 191. Matter, A. Drug Discovery Today 2001, 6, 1005.
6. Naruse, N.; Kageyama-Kawase, R.; Funahashi, Y.; Wakabayashi, T.; Watanabe, Y.; Sameshima T.; Dobashi, K. J. Antibiot. 2000, 53, 579.
7. Wakabayashi, T.; Kageyama-Kawase, R.; Naruse, N.; Funahashi Y.; Yoshimatsu, K. J. Antibiot. 2000, 53, 591.
8. 2 and UCS15A.
9. (a) Sharma, S. V.; Oneyama, C.; Yamashita, Y.; Nakano, H.; Sugawara, K.; Hamada, M.; Kosaka N.; Tamaoki, T. Oncogene 2001, 20, 2068.
10. (b) Oneyama, C.; Nakano H.; Sharma, S. V. Oncogene 2002, 21, 2037.
11. (c) Oneyama, C.; Agatsuma, T.; Kanda, Y.; Nakano, H.; Sharma, S. V.; Nakano, S.; Narazaki, F.; Tatsuta, K. Chem. Biol. 2003, 10, 443.
12. Tatsuta, K.; Nakano, S.; Narazaki, F.; Nakamura, Y. Tetrahedron Lett. 2001, 42, 7625.
13. Shotwell, J. B.; Krygowski, E. S.; Hines, J.; Koh, B.; Huntsman, E. W. D.; Choi, H. W.; Schneekloth, J. S.; Wood J. L.; Crews, C. M. Org. Lett. 2002, 4, 3087. Fang, F.; Johannes, C.; Yao Y.; Zhu, X. Patent Appl. WO 03/057685, 2003.
14. Shotwell, J. B.; Krygowski, E. S.; Hines, J.; Koh, B.; Huntsman, E. W. D.; Choi, H. W.; Schneekloth, J. S.; Wood J. L.; Crews, C. M. Org. Lett. 2002, 4, 3087. Fang, F.; Johannes, C.; Yao Y.; Zhu, X. Patent Appl. WO 03/057685, 2003.
15. Saimoto, H.; Yoshida, K.; Murakami, T.; Morimoto, M.; Sashiwa H.; Shigemasa, Y. J. Org. Chem. 1996, 61, 6768.
16. Evans, D. A.; Rieger, D. L.; Bilodeau, M. T.; Urpi, F. J. Am. Chem. Soc. 1991, 113, 1047. Yoshida, Y.; Hayashi, R.; Sumihara, H.; Tanabe, Y. Tetrahedron Lett. 1997, 38, 8727.
17. Evans, D. A.; Rieger, D. L.; Bilodeau, M. T.; Urpi, F. J. Am. Chem. Soc. 1991, 113, 1047. Yoshida, Y.; Hayashi, R.; Sumihara, H.; Tanabe, Y. Tetrahedron Lett. 1997, 38, 8727.
18. 2) was 0.1660. Some disorder was observed in the alkenyl chain, which was modeled in two equal occupancy orientations.
19. Kocienski, P. J. Protecting Groups; Thieme: Stuttgart, 1994.
20. Aldol reactions using triol 5 were unsuccessful. Other protecting groups (MOM, Bn, and allyl) for the simultaneous protection of the C-2 and C-6 phenolic groups were examined, but these proved to be less practical.
21. Whatmore, J. L.; Swann, E.; Barraja, P.; Newsome, J. J.; Bunderson, M.; Beall, H. D.; Tooke, J. E.; Moody, C. J. Angiogenesis 2002, 5, 45.
22. Mosmann, T. J. Immunol. Methods 1983, 65, 55.
23. Fletcher, D. A.; McMeeking R. F.; Parkin, D. J. Chem. Inf. Comput. Sci. 1996, 36, 746.