A novel strategy for the synthesis of medium-sized lactams

Organic Letters

Volumn 4, Issue 16, 2002, Pages 2673-2674

  Bieräugel, Hans ^a   Jansen, T Paul ^a   Schoemaker, Hans E ^a,b   Hiemstra, Henk ^a   Van Maarseveen, Jan H ^a  

^a UNIVERSITY OF AMSTERDAM   (Netherlands)

^b DSM RESEARCH   (Netherlands)

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[No Author keywords available]

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ARTICLE;

EID: 2442657224     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0261579     Document Type: Article

References (21)

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2. (b) Evans, P. A.; Holmes, A. B. Tetrahedron 1991, 47, 9131.
3. For some earlier work on difficult lactamizations, see: (a) Steliou, K.; Poupart, M.-A. J. Am. Chem. Soc. 1983, 105, 7130.
4. (b) Mader, M.; Helquist, P. Tetrahedron Lett. 1988, 29, 3049.
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16. (d) Zhu, S. S.; Cefalo, D. R.; La, D. S.; Jamieson, J. Y.; Davis, W. M.; Hoveyda, A. H.; Schrock, R. R. J. Am. Chem. Soc. 1999, 121, 8251.
17. (e) Wheaterhead, G. S.; Ford, J. G.; Alexanian, E. J.; Schrock, R. R.; Hoveyda, A. H. J. Am. Chem. Soc. 2000, 122, 1828.
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19. Especially in the case of the six-membered lactam, conducting the final lactamization reaction at a higher concentration also gave the dimeric 12-membered bislactam. At 0.01 M the content of dimer was <5%.
20. 2) resulted in full recovery of the starting material.
21. For an excellent review on modern approaches towards cyclic peptides, see: Lambert, J. N.; Mitchell, J. P.; Roberts, K. D. J. Chem. Soc. Perkin Trans. 1 2001, 471.