Design, synthesis, and x-ray crystallographic analysis of two novel spirolactam systems as. beta.-turn mimics

…, WB Gleason, RL Johnson

Index: Genin, Michael J.; Gleason, William B.; Johnson, Rodney L. Journal of Organic Chemistry, 1993 , vol. 58, # 4 p. 860 - 866

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Citation Number: 57

Abstract

Two novel 5.4-spirolactam systems have been developed as@-turn mimics. The (R)-5.4- spirolactam system of 4 was designed to mimic the type-I1 &turn, and the (S)-5.4-spirolactam system of 5 was designed to mimic the type-11'@-turn. The 5.4-spirolactam dipeptide mimic 11 was synthesized in racemic form from pipecolic acid. This intermediate was then converted to the diastereoisomeric mixture of peptidomimetics 4 and 5, which were ...