Highly efficient synthesis of medium-sized lactams via intramolecular Staudinger-aza-Wittig reaction of ω-azido pentafluorophenyl ester: Synthesis and biological evaluation of LY411575 analogues

Tetrahedron Letters

Volumn 45, Issue 11, 2004, Pages 2323-2326

  Fuwa, Haruhiko ^a   Okamura, Yumiko ^a   Morohashi, Yuichi ^a   Tomita, Taisuke ^a   Iwatsubo, Takeshi ^a   Kan, Toshiyuki ^a   Fukuyama, Tohru ^a   Natsugari, Hideaki ^a  

^a UNIVERSITY OF TOKYO   (Japan)

Author keywords

Aza Wittig reaction; Medium sized lactams; Staudinger reaction; Structure activity relationship; Secretase inhibitor

Indexed keywords

GAMMA SECRETASE INHIBITOR; LACTAM DERIVATIVE; LY 411575; PHENYL GROUP; UNCLASSIFIED DRUG;

ARTICLE; CHROMATOGRAPHY; CONTROLLED STUDY; DRUG ACTIVITY; DRUG SCREENING; HUMAN; HUMAN CELL; MOLECULAR INTERACTION; STAUDINGER REACTION; STRUCTURE ACTIVITY RELATION; WITTIG REACTION;

EID: 1242270589     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2004.01.087     Document Type: Article

References (30)

1. For recent reviews see: Schmidt B. Chem. Bio. Chem. 4:2003;366.
2. Wolfe M.S., Haass C. J. Biol. Chem. 276:2001;5413.
3. Steiner H., Haass C. Nat. Rev. Mol. Cell Biol. 1:2000;217.
4. Sisodia S.S., Annaert W., Kim S.-H., De Strooper B. Trends Neurosci. 24:2001;52.
5. Tsai J.-Y., Wolfe M.S., Xia W. Curr. Med. Chem. 9:2002;1087.
6. Ghosh A.K., Hong L., Tang J. Curr. Med. Chem. 9:2002;1135.
7. Wolfe M.S. J. Med. Chem. 44:2001;2039.
8. Lewis H.D., Perez Revuelta B.I., Nadin A., Neduvelil J.G., Harrison T., Pollack S.J., Shearman M.S. Biochemistry. 42:2003;7580.
9. Wu, J.; Tung, J. S.; Thorsett, E. D.; Pleiss, M. A.; Nissen, J. S.; Neitz, J.; Latimer, L. H.; John, V.; Freedman, S.; Britton, T. C.; Audia, J. E. ; Reel, J. K.; Mabry, T. E.; Dressman, B. A.; Cwi, C. L.; Droste, J. J.; Henry, S. S.; McDaniel, S. L.; Scott, W. L.; Stucky, R. D.; Porter, W. J. PCT Int. Appl., WO9828268.
10. Staudinger H., Meyer J. Helv. Chim. Acta. 2:1919;635.
11. Gololobov Y.G., Kasukhin L.F. Tetrahedron. 48:1992;1353.
12. Molina P., Vilaplana M.J. Synthesis. 1994;1197.
13. Eguchi E., Matsushita Y., Yamashita K. Org. Prep. Proced. 24:1992;209.
14. Very recently van Maarseveen and co-workers have reported an intramolecular Staudinger ligation method for the construction of medium-sized lactams. See: David O., Meester W.J.N., Bieräugel H., Schoemaker H.E., Hiemstra H., van Maarseveen J.H. Angew. Chem., Int. Ed. 42:2003;4373.
15. Kurosawa W., Kan T., Fukuyama T. J. Am. Chem. Soc. 125:2003;8112.
16. Suzuki A., Miyaura N. Chem. Rev. 95:1995;2457.
17. Suzuki A. J. Organomet. Chem. 576:1999;147.
18. Penhoat M., Levacher V., Dupas G. J. Org. Chem. 68:2003;9517.
19. Baudoin O., Cesario M., Guénard D., Guritte F. J. Org. Chem. 67:2002;1199.
20. Baudoin O., Guénard D., Guritte F. J. Org. Chem. 65:2000;9268.
21. In contrast to our previous result (Ref. 6) all medium-sized lactams synthesized in the present study ( 17-22 ) could be directly isolated without conducting hydrolysis separately.
22. We have found that use of trifuluoroacetic acid (TFA) as a co-solvent was crucial for clean reduction of oximes. For a related example see: Negi S., Matsukura M., Mizuno M., Miyake K., Minami N. Synthesis. 1996;991.
23. Hanessian S., Liak T.J., Vanasse B. Synthesis. 1981;396.
24. Patricelli M.P., Cravatt B.F. Biochemistry. 40:2001;6107.
25. Tamiaki H., Kiyomori A., Maruyama K. Bull. Chem. Soc. Jpn. 66:1993;1768.
26. Takahashi Y., Hayashi I., Tominari Y., Rikimaru K., Morohashi Y., Kan T., Natsugari H., Fukuyama T., Tomita T., Iwatsubo T. J. Biol. Chem. 278:2003;18664.
27. Takasugi N., Tomita T., Hayashi I., Tsuruoka M., Niimura M., Thinakaran G., Takahashi Y., Iwatsubo T. Nature. 422:2003;438.
28. Each analogue was synthesized as a 1:1 mixture of diastereomers and used in the assay without separation.
29. The carbon numbering in this paper is according to Ref. [2b].
30. Kan T., Tominari Y., Morohashi Y., Natsugari H., Tomita T., Iwatsubo T., Fukuyama T. Chem. Commun. 2003;2244.