New stereospecific synthesis of Tesaglitazar and Navaglitazar precursors

Tetrahedron Asymmetry

Volumn 20, Issue 23, 2009, Pages 2694-2698

  Brenna, Elisabetta ^a   Fuganti, Claudio ^a   Gatti, Francesco G ^a   Parmeggiani, Fabio ^a  

^a POLITECNICO DI MILANO   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

2 ALLYOXY 3 (4 METHOXYPHENYL)ACRYLALDEHYDE; 2 ETHOXY 3 (4 METHOXYPHENYL)ACRYLALDEHYDE; 2 METHOXY 3 (4 METHOXYPHENYL)ACRYLALDEHYDE; 3 (4 METHOXYPHENYL) 1,2 PROPANDIOL; ALCOHOL DERIVATIVE; CINNAMALDEHYDE DERIVATIVE; ESTER DERIVATIVE; ETHYL ALPHA ALKOXY PHENYLPROPANOATE ESTER DERIVATIVE; NAVAGLITAZAR; ORAL ANTIDIABETIC AGENT; TESAGLITAZAR; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; CLAISEN CONDENSATION; DRUG STRUCTURE; ENANTIOMER; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; REDUCTION; STEREOCHEMISTRY;

EID: 76449108660     PISSN: 09574166     EISSN: 1362511X     Source Type: Journal    
DOI: 10.1016/j.tetasy.2009.10.027     Document Type: Article

References (24)

1. Brenna, E.; Fuganti, C.; Gatti, F. G.; Parmeggiani, F. Tetrahedron: Asymmetry 2009, doi:10.1016/j.tetasy.2009.10.013.
2. Anderson, K. PCT Appl. WO 99/62872.
3. Martin J.A., Brooks D.A., Prieto L., Gonzalez R., Torrado A., Rojo I., Lopez de Uralde B., Lamas C., Ferrito M., Martin-Ortega M.D., Agejas J., Parra F., Rizzo J.R., Rhodes G.A., Robey R.L., Alt C.A., Wendel S.R., Zhang T.Y., Reifel-Miller A., Montrose-Rafidazeh C., Brozinik J.T., Hawkins E., Misener E.A., Briere D.A., Ardecky R., Fraser J.D., and Warshawsky A.M. Bioorg. Med. Chem. Lett. 15 (2005) 51-55
4. For an asymmetric synthesis of 1 by catalytic reduction of α-ethoxy cinnamic acid, see: Woltering, M.; Bunlakasnanusorn, T.; Gerlach, A. PCT Appl. US 2007/0149804.
5. Houpis I.N., Patterson L.E., Alt C.A., Zhang T.Y., and Haurez M. Org. Lett. 7 (2005) 1947-1950
6. For a review on baker's yeast see:. Servi S. Synthesis (1990) 1-25
7. Dao D.H., Okamura M., Akasaka T., Kawai Y., Hida K., and Ohno A. Tetrahedron: Asymmetry 9 (1998) 2725-2737
8. Zhou B.-N., Gopalan A.S., VanMiddlesworth F., Shieh W.-R., and Sih C.J. J. Am. Chem. Soc. 105 (1983) 5925-5926
9. Gopalan A.S., and Jacobs H.K. J. Chem. Soc., Perkin Trans. 1 (1990) 1897-1900
10. Bernier D., Moser F., and Brückner R. Synthesis (2007) 2240-2248
11. Linderberg M.T., Moge M., and Sivadasan S. Org. Process Res. Dev. 8 (2004) 838-845
12. Storz T., Dittmyr P., Fauquez P.F., Marschal P., Lottenbach W.U., and Steiner H. Org. Process Res. Dev. 7 (2003) 559-570
13. Partial isomerisation of the double bond occurred during the aldehyde formation reaction.
14. Fuganti C., and Grasselli P. J. Chem. Soc., Perkin Trans. 1 (1983) 241-244
15. For some examples of baker's yeast mediated reductions of α,β-unsaturated aldehydes adsorbed on solid support see:. D'Arrigo P., Fuganti C., Pedrocchi Fantoni G., and Servi S. Tetrahedron 54 (1998) 15017-15026
16. Fuganti C., Serra S., and Dulio C. J. Chem. Soc., Perkin Trans. 1 (1999) 279-282
17. Serra S., Gatti F.G., and Fuganti C. Eur. J. Org. Chem. (2008) 1036-1037
18. De Mico A., Margarita R., Parlanti L., Vescovi A., and Piancatelli G. J. Org. Chem. 62 (1997) 6974-6977
19. Narina S.V., Kumar T.S., George S., and Sudalai A. Tetrahedron Lett. 48 (2007) 65-68
20. Milicevic S., Matovic R., and Saicic R.N. Tetrahedron Lett. 45 (2004) 955-957
21. Hand E.S., Belmore K.A., and Kispert L.D. Helv. Chim. Acta 76 (1993) 1928-1938
22. Aitken R.A., and Thom G.L. Synthesis (1989) 958-959
23. Smith III A.B., Rivero R.A., Hale K.J., and Vaccaro H.A. J. Am. Chem. Soc. 113 (1991) 2092-2112
24. Belleau B., Gulini U., Gour-Salen B., and Ahmed F.R. Can. J. Chem. 63 (1985) 1268-1274