Controlling chemoselectivity-application of DMF di-t-butyl acetal in the regioselective synthesis of 3-monosubstituted indolizines

Tetrahedron Letters

Volumn 47, Issue 50, 2006, Pages 8817-8820

  Xia, Zhiqiang ^a   Przewloka, Teresa ^a   Koya, Keizo ^a   Ono, Mitsunori ^a   Chen, Shoujun ^a   Sun, Lijun ^a  

^a Synta Pharmaceuticals Corp   (United States)

Author keywords

DMF di t butyl acetal; Indolizine; Picolinium salt; Regioselective synthesis

Indexed keywords

ACETAL DERIVATIVE; INDOLIZINE DERIVATIVE; N,N DIMETHYLFORMAMIDE; PICOLINE DERIVATIVE;

ACYLATION; ARTICLE; CYCLIZATION; DRUG SYNTHESIS; SUBSTITUTION REACTION;

EID: 33750631868     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2006.10.052     Document Type: Article

References (21)

1. Gubin J., Vogelaer H., Inion H., Houben C., Luccetti J., Mahaux J., rosseels G., Peren M., Clinet M., Polster P., and Chatelain P. J. Med. Chem. 36 (1993) 1425
2. Hagishita S., Yamada M., Shirahase K., Okada T., Murakami Y., Ito Y., Matsuura T., Wada M., Kato T., Ueno M., Chikazawa Y., Yamada K., Ono T., Teshirogi I., and Ohtani M. J. Med. Chem. 39 (1996) 3636
3. Chai W., Breitenbucher J.G., Kwok A., Li X., Wong V., Carruthers N.I., Lovenberg T.W., Mazur C., Wilson S.J., Axe F.U., and Jones T.K. Bioorg. Med. Chem. Lett. 13 (2003) 1767
4. Bermudez J., Fake C.S., Joiner G.F., Joiner K.A., Km F.D., Miner W.D., and Sanger G.J. J. Med. Chem. 33 (1990) 1924-1929
5. Hodgkiss R.J., Middleton R.W., Parrick J., Rami H.K., Wardman P., and Wilson G.D. J. Med. Chem. 35 (1992) 1920
6. For a recent review,. Shipman M. Sci. Synth. 10 (2001) 745
7. Katrisky A.R., Qiu G., Yang B., and He H.-Y. J. Org. Chem. 64 (1999) 7618
8. Bora U., Saikia A., and Boruah R.C. Org. Lett. 5 (2003) 435-438
9. Kim M., and Vedejs E. J. Org. Chem. 69 (2004) 6945
10. Matsuda Y., Kahra S., Katou K., Uenura T., and Tamashita K. Heterocycles 60 (2003) 405
11. De Bue G., and Nasielski J. Bull. Soc. Chim. Belg. 106 (1997) 97
12. Bonneau R., Romashin Y.N., Liu M.T.H., and MacPherson S.E. J. Chem. Soc., Chem. Commun. (1994) 509
13. Boekelheide W. J. Am. Chem. Soc. 81 (1959) 1456
14. Sawada K., Okada S., Kurda A., Watanabe S., Sawada Y., and Tanaka H. Chem. Pharm. Bull. 49 (2001) 799
15. Kel'in A.V., Sromek A.W., and Gevorgyan V. J. Am. Chem. Soc. 123 (2001) 2074-2075
16. Park C.-H., Ryabova V., Seregin I.V., Sromek A.W., and Gevorgyan V. Org. Lett. 6 (2004) 1159-1162
17. Kaloko Jr. J., and Hayford A. Org. Lett. 7 (2005) 4305
18. Chichibabin A.E., and Stepanov F.N. Chem. Ber. 62B (1929) 1068
19. Copar A., Stanovnik B., and Tisler M. J. Heterocycl. Chem. 30 (1993) 1577
20. We were particularly interested in the regioselective synthesis of 3-(4-cyanobenzoyl)indolizine as it was the key intermediate of the clinical candidate, STA-5312. The discovery and process development that led to the successful multi-kilogram scale manufacturing of STA-5312 will be disclosed elsewhere.
21. Miki Y., Kinoshita H., and Yoshimaru T. Heterocycles 26 (1987) 199-204