Design, synthesis, and conformational analysis of a proposed type I β-turn mimic

…, PR Kym, JA Katzenellenbogen

Index: Fink, Brian E.; Kym, Phil R.; Katzenellenbogen, John A. Journal of the American Chemical Society, 1998 , vol. 120, # 18 p. 4334 - 4344

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Citation Number: 114

Abstract

In an effort to design a dipeptide structural mimic of protein and peptide β-turns, we have prepared and evaluated the conformation of derivatives of the novel, highly constrained ten- membered lactam,(3 S, 10 S)-(6 E)-2-azacyclodec-6-enone (1). A synthetic route utilizing ring-closing olefin metathesis (RCM) has been used to prepare this novel ten-membered ring in high yield. X-ray crystallography and 1H NMR analysis have established that ring ...