Application of tandem Ugi reaction/ring-closing metathesis in multicomponent synthesis of unsaturated nine-membered lactams

Tetrahedron Letters

Volumn 44, Issue 41, 2003, Pages 7655-7658

  Banfi, Luca ^a   Basso, Andrea ^a   Guanti, Giuseppe ^a   Riva, Renata ^a  

^a UNIVERSITY OF GENOA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

LACTAM DERIVATIVE;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL REACTION; DRUG SYNTHESIS; ELECTRIC POTENTIAL; INFRARED SPECTROSCOPY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; RING CLOSING METATHESIS; STEREOCHEMISTRY; UGI REACTION;

EID: 0141741234     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2003.08.027     Document Type: Article

References (35)

1. Haubner R., Finsinger D., Kessler H. Angew. Chem., Int. Ed. Engl. 36:1997;1375-1389.
2. Dechantsreiter M.A., Planker E., Mathä B., Lohof E., Hölzemann G., Jonczyk A., Goodmann S.L., Kessler H. J. Med. Chem. 42:1999;3033-3040.
3. Golebiowski A., Jozwik J., Klopfenstein S.R., Colson A.O., Grieb A.L., Russell A.F., Rastogi V.L., Diven C.F., Portlock D.E., Chen J.J. J. Comb. Chem. 4:2002;584-590.
4. Hanessian S., McNaughton-Smith G., Lombart H.-G., Lubell W.D. Tetrahedron. 38:1997;12789-12854.
5. Belvisi L., Bernardi A., Checchia A., Manzoni L., Potenza D., Scolastico C., Castorina M., Cupelli A., Giannini G., Carminati P., Pisano C. Org. Lett. 3:2001;1001-1004.
6. Belvisi L., Caporale A., Colombo M., Manzoni L., Potenza D., Scolastico C., Castorina M., Cati M., Giannini G., Pisano C. Helv. Chim. Acta. 85:2002;4353-4368.
7. Freidinger R.M. J. Org. Chem. 50:1985;3631-3633.
8. Piscopio A.D., Miller J.F., Koch K. Tetrahedron. 55:1999;8189-8198.
9. Weber K., Ohnmacht U., Gmeiner P. J. Org. Chem. 65:2000;7406-7416.
10. Fink B.E., Kym P.R., Katzenellenbogen J.A. J. Am. Chem. Soc. 120:1998;4334-4344.
11. Vo-Thanh G., Boucard V., Sauriat-Dorizon H., Guibé F. Synlett. 2001;37-40.
12. Creighton C.J., Reitz A.B. Org. Lett. 3:2001;893-895.
13. Wilson S.R., Sawicki R.A. J. Heterocycl. Chem. 19:1982;81-83.
14. Kahn M., Devens B. Tetrahedron Lett. 27:1986;4841-4844.
15. Evans P.A., Holmes A.B., Russell K. Tetrahedron Lett. 33:1992;6857-6858.
16. Wilson S.R., Sawicki R.A. J. Org. Chem. 44:1979;330-336.
17. Hoffmann T., Waibel R., Gmeiner P. J. Org. Chem. 68:2003;62-69.
18. i+3 was found. The epimer of 7 also turned out to be generally less stable and more flexible than 7.
19. 15.
20. Mohamadi F., Richards N.G.J., Guida W.C., Liskamp R., Lipton M., Caufield C., Chang G., Hendrickson T., Still W.C. J. Comput. Chem. 11:1990;440-467.
21. Ponder J.W., Richards F.M. J. Comput. Chem. 8:1989;1016-1024.
22. Chang G., Guida W.C., Still W.C. J. Am. Chem. Soc. 111:1989;4379-4386.
23. Still W.C., Tempczyk A., Hawley R.C., Hendrickson T. J. Am. Chem. Soc. 112:1990;6127-6129.
24. Dömling A., Ugi I. Angew. Chem., Int. Ed. 39:2000;3169-3210.
25. Dömling A. Curr. Opin. Chem. Biol. 6:2002;306-313.
26. Trnka T.M., Grubbs R.H. Acc. Chem. Res. 34:2001;18-29.
27. Fürstner A. Angew. Chem., Int. Ed. 39:2000;3012-3043.
28. 2, -30°C, 92%.
29. 20 In our hands the yields were not higher than 40%.
30. Schöllkopf U., Hoppe D., Jentsch R. Chem. Ber. 108:1975;1580-1592.
31. In some cases by using MeOH and isocyanide 3 we observed various degrees of transesterification. Thus we now prefer to use EtOH for reactions involving 3 .
32. 13C NMR, IR, GC-MS (when possible) and elemental analysis.
33. While the two diastereoisomers were usually well separated by silica gel chromatography using petroleum ether/AcOEt eluents (with the exceptions of 6h and 6i ), complete removal of intermolecular products was in some cases troublesome and required 2-3 subsequent chromatographies with different eluents.
34. 4 group prefers a pseudo-equatorial position in both epimers, as demonstrated by the high J (9-10 Hz) between NH and CH-N. Thus in the cis compound the methyl group is pseudo-axial and lies at a close distance with one of the H-4. All these results fit well with the expected (Macromodel and Chem3D) preferred conformations.
35. 13C C-5: trans: 32.91-33.68; cis: 29.60-30.92. C-6: trans: 124.02-124.19; cis: 122.55-122.85. C-7: trans: 134.21-134.46; cis: 134.90-135.35. The methyl at C-3 is always upfield for trans isomers by 0.5-1. 75 ppm. C-4 is always downfield for trans isomers. C-8 is always upfield for trans isomers by 0.60-0.93 ppm. C-9 is always downfield for trans isomers by 0.42-0.55 ppm.