ChemInform Abstract: Practical Stereoselective Synthesis of Conformationally Constrained Unnatural Proline-Based Amino Acids and Peptidomimetics.
Abstract
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ChemInform Abstract
Both trans- and cis-fused esters (VII) and (IX) are prepared by a route involving the allylation of a diastereomeric mixture of alcohol (II) affording trans-diallyl derivative (IV) predominantly, and the ring-closing metathesis of diallylated products (IV) and (V) to give after hydrogenation the target unnatural amino acid esters. Regioselective electrochemical oxidation at the 7a position of the indole nucleus of cis ester (IX) followed by allylation provides derivative (XII) which allows the synthesis of trinuclear dipeptide mimics (XIV) and (XV).
