New strategy for the synthesis of phosphatase inhibitors TMC-69-6H and analogs

Tetrahedron Letters

Volumn 47, Issue 52, 2006, Pages 9305-9308

  Brondel, Nicolas ^a   Renoux, Brigitte ^a   Gesson, Jean Pierre ^a  

^a UMR 6514   (France)

Author keywords

Antitumor activity; Diastereoselective aldolization; Metathesis; PTP1B inhibitor; TMC 69 6H

Indexed keywords

ANTINEOPLASTIC AGENT; ENZYME INHIBITOR; PHOSPHATASE; PYRAN; TMC 69 6H; UNCLASSIFIED DRUG;

ALDOL REACTION; ARTICLE; CHEMICAL ANALYSIS; CHEMICAL PROCEDURES; DRUG SYNTHESIS; RING CLOSING METATHESIS;

EID: 33751188488     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2006.10.102     Document Type: Article

References (23)

1. Hirano N., Khono J., Tsunoda S., Nishio M., Kishi N., Okuda T., Kawano K., Komatsubara S., and Nakanishi N. J. Antibiot. 54 (2001) 421-427
2. Kohno J., Hirano N., Sugawara K., Nishio M., Hashiyama T., Nakanishi N., and Komatsubara S. Tetrahedron 57 (2001) 1731-1735
3. Fürstner A., Feyen F., Prinz H., and Waldmann H. Angew. Chem., Int. Ed. 42 (2003) 5361-5364
4. Fürstner A., Feyen F., Prinz H., and Waldmann H. Tetrahedron 60 (2004) 9543-9558
5. Elchebly M., Payette P., Michaliszyn E., Cromlish W., Collins S., Loy A.L., Normandin D., Cheng A., Himms-Hagen J., Chan C.C., Ramachandran C., Gresser M., Tremblay M.L., and Kennedy B.P. Science 283 (1999) 1544-1548
6. Moller N.P., Iversen L.F., Andersen H.S., and McCormack J.G. Curr. Opin. Drug Discovery 3 (2000) 527-540
7. Shenolicar S. Annu. Rev. Cell Biol. 10 (1994) 55-86
8. Davis S.J., Elvidge J.A., and Foster A.B. J. Chem. Soc. (1962) 3638-3644
9. Mohamed E. A.; Abdel-Rahman R. M.; Tawfik A. M.; Ismail M. M. CAN 121:83299 AN 1994:483299 CAPLUS.
10. Sato T., Yoshimatsu K., and Otera J. Synlett (1995) 845-846
11. McGee K.F., Al-Tel T.H., and Sieburth S.McN. Synthesis 8 (2001) 1185-1196
12. Comins D.L., and Jianhua G. Tetrahedron Lett. 35 (1994) 2819-2822
13. Thadani A.N., and Batey R.A. Org. Lett. 4 (2002) 3827-3830
14. Batey R.A., Thadani A.N., and Smil D.V. Tetrahedron Lett. 40 (1999) 4289-4292
15. Roush W.R., Adam M.A., Walts A.E., and Harris D.J. J. Am. Chem. Soc. 108 (1986) 3422-3434
16. Kim J.N., and Ryu E.K. Synth. Commun. 26 (1996) 67-74
17. Kinoshita A., and Mori M. Synlett (1994) 1020-1022
18. Sanford M.S., Love J.A., and Grubbs R.H. J. Am. Chem. Soc. 123 (2001) 6543-6554
19. Cavallo L. J. Am. Chem. Soc. 124 (2002) 8965-8973
20. Guo H., Madhushaw R., Shen F.M., and Liu R.S. Tetrahedron 58 (2002) 5627-5637
21. Diver S.T., and Giessert A.J. Chem. Rev. 104 (2004) 1317-1382
22. Blackwell H.E., O'Leary D.J., Chatterjee A.K., Washenfelder R.A., Bussmann D.A., and Grubbs R.H. J. Am. Chem. Soc. 122 (2000) 58-71
23. 2: 0.83-0.85 (m, 9H), 1.11-1.63 (m, 15H), 1.77 (1H, br d), 2.08 (m, 1H), 3.72 (dd, 1H, 11.6, 2.5), 3.96 (br d, 11.6), 4.68 (d, 10.5, 1H), 7.35 (m, 1H), 7.41 (m, 2H), 7.46 (m, 2H), 9.51 (br s, 1H).