Waibel R, Gmeiner P (2003)
Publication Type: Journal article
Publication year: 2003
Publisher: American Chemical Society
Book Volume: 68
Pages Range: 62-69
DOI: 10.1021/jo0261653
Starting from natural α-amino acids, a practical synthesis of the dehydro-Freidinger lactams 9a-h based on the ring-closing olefin metathesis reaction was investigated. The presented examples comprise 6-, 7-, 8-, 9-, and 10-membered cyclic dipeptide mimics. Structural variations were demonstrated. We approached the metathesis precursors 8a-h employing an N-alkylation/peptide-coupling strategy. Subsequent ring closure was promoted by the ruthenium-based catalyst 10a or 10b. The resulting tetraresidue 11d was shown to undergo intramolecular hydrogen bonding based on NMR and FT-IR studies. Thus, the development of dehydro-Freidinger lactams as potential reverse turn inducers stabilizing an intramolecular NH i+3⋯CO i hydrogen-bond was demonstrated.
APA:
Waibel, R., & Gmeiner, P. (2003). A General Approach to Dehydro-Freidinger Lactams: Ex-Chiral Pool Synthesis and Spectroscopic Evaluation as Potential Reverse Turn Inducers. Journal of Organic Chemistry, 68, 62-69. https://doi.org/10.1021/jo0261653
MLA:
Waibel, Reiner, and Peter Gmeiner. "A General Approach to Dehydro-Freidinger Lactams: Ex-Chiral Pool Synthesis and Spectroscopic Evaluation as Potential Reverse Turn Inducers." Journal of Organic Chemistry 68 (2003): 62-69.
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