Solid phase organic synthesis of piperazinone containing enkephalin mimetics: a readily derivatized, traceless scaffold |
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Authors: | Shreder K Zhang L Gleeson J P Ericsson J A Yalamoori V V Goodman M |
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Institution: | Department of Chemistry, University of California at San Diego, La Jolla 92093-0343, USA. |
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Abstract: | The solid phase synthesis of a series of piperazinone-derived Leu-enkephalin analogues is presented. The initial step in the synthesis involved the N-alkylation of Wang resin bound N-(4-tert-butyloxy-phenethyl)-glycine with D or L Boc-serine-beta-lactone (the Vederas lactone). The resulting carboxylic acid was then coupled to a variety of monosubstituted benzylamine derivatives using benzotriazol-1-yloxy-tris(dimethyl-amino)phosphonium hexafluorophosphate (the BOP reagent) to yield a series of resin bound tertiary amides. Treatment with 5% H2O in TFA resulted in the facile cleavage, deprotection, and cyclization of this linear precursor to yield a series of piperazinones (compounds 1-8). |
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