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