ol026182e_si_001.pdf (998.99 kB)
On the Verge of Axial Chirality: Atroposelective Synthesis of the AB-Biaryl Fragment of Vancomycin†,‡
journal contribution
posted on 2002-07-27, 00:00 authored by Gerhard Bringmann, Dirk Menche, Jörg Mühlbacher, Matthias Reichert, Nozomi Saito, Steven S. Pfeiffer, Bruce H. LipshutzUsing the “lactone concept”, differently substituted AB-biaryl fragments (P)-2 (R = Me, t-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 (M)-29.
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.