Tetrahedron Letters p. 221 - 224 (1998)
Update date:2022-07-31
Topics:
Shreder, Kevin
Zhang, Li
Goodman, Murray
The synthesis of a constrained, piperazinone analog of Leu-enkephalin is presented. A key step in this synthesis was the use of the secondary amine, Boc-Tyr(OtBu)Ψ[CH2NH]Gly-OMe, to ring open the β-lactone of Z-protected L-serine (the Vederas lactone). The resulting free acid was then coupled to H-Phe-Leu-OtBu in a one-pot fashion using standard carbodiimide coupling conditions. This linear precursor cyclized upon hydrogenolysis of the Z group to form the N4-substituted, 6-carboxy-derived piperazinone (5). Deprotection of compound 5 using 1:1 TFA:CH2Cl2 yielded the target compound 1.
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