On the Verge of Axial Chirality:  Atroposelective Synthesis of the AB-Biaryl Fragment of Vancomycin<sup>†</sup><sup>,</sup><sup>‡</sup> Gerhard Bringmann Dirk Menche Jörg Mühlbacher Matthias Reichert Nozomi Saito Steven S. Pfeiffer Bruce H. Lipshutz 10.1021/ol026182e.s001 https://acs.figshare.com/articles/journal_contribution/On_the_Verge_of_Axial_Chirality_Atroposelective_Synthesis_of_the_AB-Biaryl_Fragment_of_Vancomycin_sup_sup_sup_sup_sup_sup_/3743205 Using the “lactone concept”, differently substituted AB-biaryl fragments (<i>P</i>)-2 (R = Me, <i>t</i>-Bu) of vancomycin have been synthesized atroposelectively. Their otherwise configurational instability was remedied by inclusion of two chlorine atoms in the B ring to give (<i>M</i>)-<b>29</b>. Starting from a still configurationally unstable lactone-bridged precursor, we obtained this biaryl with high atroposelectivity (dr 94:6) by ring cleavage with dynamic kinetic diastereomeric resolution. 2002-07-27 00:00:00 inclusion atroposelectivity Chirality Axial concept biaryl vancomycin chlorine atoms Fragment dr atroposelectively Bu B ring lactone Synthesi configurationally Atroposelective fragment diastereomeric resolution configurational instability ring cleavage Vancomycin precursor Verge