This study reveals an alternative sequence for the synthesis of compounds that contain the pyrrolodiketopiperazine structural motif. Starting with a diketopiperazine precursor, a mild aldol condensation precedes pyrrole annulation and bicyclic ring fusion. The derived intermediate aldol condensation products, which bear either a protected carbonyl or a functionalized alkyne, can be cyclized to the pyrrolodiketopiperazine by protic or gold Lewis acid catalysis.
This study reveals an alternative sequence for the synthesis of compounds that contain the pyrrolodiketopiperazine structural motif. Starting with a n class="Chemical">diketopiperazine precursor, a mild aldol condensation precedes pyrrole annulation and bicyclic ring fusion. The derived intermediate aldol condensation products, which bear either a protected carbonyl or a functionalized alkyne, can be cyclized to the pyrrolodiketopiperazine by protic or gold Lewis acid catalysis.
Authors: Julie Miyashiro; Keith W Woods; Chang H Park; Xuesong Liu; Yan Shi; Eric F Johnson; Jennifer J Bouska; Amanda M Olson; Yan Luo; Elizabeth H Fry; Vincent L Giranda; Thomas D Penning Journal: Bioorg Med Chem Lett Date: 2009-06-13 Impact factor: 2.823