A short synthesis of the potent antitumor agent (±)- hydroxymethylacylfulvene using an allenic Pauson-Khand type cycloaddition

Journal of the American Chemical Society

Volumn 121, Issue 21, 1999, Pages 5087-5088

  Brummond, Kay M ^a   Lu, Jianliang ^a  

^a WEST VIRGINIA UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

6 HYDROXYMETHYLACYLFULVENE; ANTINEOPLASTIC AGENT; ILLUDIN M; ILLUDIN S; SESQUITERPENE DERIVATIVE; UNCLASSIFIED DRUG;

ALKYLATION; ANTINEOPLASTIC ACTIVITY; ARTICLE; CYCLIZATION; CYTOTOXICITY; DIASTEREOISOMER; DRUG STRUCTURE; DRUG SYNTHESIS; PROTEIN DNA INTERACTION; REACTION ANALYSIS;

EID: 0033516331     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja990426h     Document Type: Article

References (21)

1. (a) McMorris, T. C.; Keiner, M. J.; Wang, W.; Diaz, M. A.; Estes, L. A.; Taetle, R. Experientia 1996, 52, 75.
2. (b) McMorris, T. C.; Keiner, M. J.; Wang, W.; Yu, J.; Estes, L. A.; Taetle, R. J. Nat. Prod. 1996, 59, 896. For previous syntheses of illudin M, see the following: Kinder, F. R., Jr.; Blair, K. W. J. Org. Chem. 1994, 59, 6965; Matsumoto, T.; Shirahama, H.; Ichihara, A.; Shin, H.; Kagawa, S.; Sakan, F.; Matsumoto, S.; Nishida, S. J. Am. Chem. Soc. 1968, 90, 3280.
3. (b) McMorris, T. C.; Keiner, M. J.; Wang, W.; Yu, J.; Estes, L. A.; Taetle, R. J. Nat. Prod. 1996, 59, 896. For previous syntheses of illudin M, see the following: Kinder, F. R., Jr.; Blair, K. W. J. Org. Chem. 1994, 59, 6965; Matsumoto, T.; Shirahama, H.; Ichihara, A.; Shin, H.; Kagawa, S.; Sakan, F.; Matsumoto, S.; Nishida, S. J. Am. Chem. Soc. 1968, 90, 3280.
4. (b) McMorris, T. C.; Keiner, M. J.; Wang, W.; Yu, J.; Estes, L. A.; Taetle, R. J. Nat. Prod. 1996, 59, 896. For previous syntheses of illudin M, see the following: Kinder, F. R., Jr.; Blair, K. W. J. Org. Chem. 1994, 59, 6965; Matsumoto, T.; Shirahama, H.; Ichihara, A.; Shin, H.; Kagawa, S.; Sakan, F.; Matsumoto, S.; Nishida, S. J. Am. Chem. Soc. 1968, 90, 3280.
5. (a) McMorris, T. C.; Yu, J.; Hu, Y.; Estes, L. A.; Keiner, M. J. J. Org. Chem. 1997, 62, 3015.
6. (b) McMorris, T. C.; Kelner, M. J.; Wang, W.; Estes, L. A.; Montoya, M. A.; Taetle, R. J. Org. Chem. 1992, 57, 6876.
7. (a) Mac-Donald, J. R.; Muscoplat, C. C.; Dexter, D. L.; Mangold, G. L.; Chen, S.-F.; Keiner, M. J.; McMorris, T. C.; Von Hoff, D. D. Cancer Res. 1997, 57, 279.
8. (b) Keiner, M. J.; McMorris, T. C.; Estes, L. A.; Wang, W.; Samson, K. M.; Taetle, R. Investigational New Drugs 1996, 14, 161.
9. Keiner, M. J.; McMorris, T. C.; Estes, L.; Samson, K. M.; Bagnell, R. D.; Taetle, R. Eur. J. Cancer 1998, 34, 908.
10. Unpublished data, see the following: http://207.121.187.155/ NCI_CANCER_TRIALS/index.html. Search NCI's Trials Database (PDQ).
11. Unpublished data, see the following: http://www.mgipharma.com/mgi/ product/mgi114abs.htm
12. (a) Woynarowski, J. N.; Napier, C.; Koester, S. K.; Chen, S.-F.; Troyer, D.; Chapman, W.; MacDonald, J. R. Biochem. Pharmacol. 1997, 54, 1181.
13. (b) McMorris, T. C.; Yu, J.; Estes, L. A.; Keiner, J. Tetrahedron 1997, 53, 14579.
14. McMorris, T. C.; Hu, Y.; Yu, J.; Keiner, M. J. Chem. Commun. 1997, 315.
15. Padwa, A.; Curtis, E. A.; Sandanayaka, V. P. J. Org. Chem. 1996, 61, 73.
16. (a) Brummond, K. M.; Wan, H.; Kent, J. L. J. Org. Chem. 1998, 63, 6535.
17. (b) Brummond, K. M.; Wan, H. Tetrahedron Lett. 1998, 39, 931.
18. (c) Kent, J. L.; Wan, H.; Brummond, K. M. Tetrahedron Lett. 1995, 36, 2407.
19. Ogoshi, H.; Kikuchi, Y.; Yamaguchi, T.; Toi, H.; Aoyama, Y. Organometallics 1987, 6, 2175. 1,1-Diacetylcyclopropane was prepared from 2,4-pentanedione, 1,2-dibromoethane, and potassium carbonate in DMF.
20. Hayashi, Y.; Nishizawa, M.; Sakan, T. Tetrahedron 1977, 33, 2513.
21. Daeuble, J. F.; McGettigan, C.; Stryker, J. M. Tetrahedron Lett. 1990, 31, 2397.