Heterocyclic Compounds
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ChemInform Abstract: Synthesis of (2R,3S)-2-Hydroxymethyl-3-hydroxypyrrolidine and the Geissman-Waiss Lactone from (S)-Pyroglutamic Acid.
First published: April 25, 1989
Abstract
Starting with the protected trihydroxypyrrolidone (I) or the N-benzyldihydroxypyrrolidine (IV), the (hydroxymethyl)hydroxypyrrolidines (III) and (XVI) and the Geissman-Waiss lactone (XII) are prepared.
ChemInform Abstract
Starting with the protected trihydroxypyrrolidone (I) or the N-benzyldihydroxypyrrolidine (IV), the (hydroxymethyl)hydroxypyrrolidines (III) and (XVI) and the Geissman-Waiss lactone (XII) are prepared. Alkylation of (XII) with ethyl bromoacetate (XIII) yields the amino acid ester (XIV). In contrast to the diol (IV), the diastereomer (XVI) cannot be converted into the nitrile (XVII).
