10.1021/ol026182e.s001
Gerhard Bringmann
Gerhard
Bringmann
Dirk Menche
Dirk
Menche
Jörg Mühlbacher
Jörg
Mühlbacher
Matthias Reichert
Matthias
Reichert
Nozomi Saito
Nozomi
Saito
Steven S. Pfeiffer
Steven S.
Pfeiffer
Bruce H. Lipshutz
Bruce H.
Lipshutz
On the Verge of Axial Chirality:
Atroposelective Synthesis of the
AB-Biaryl Fragment of Vancomycin<sup>†</sup><sup>,</sup><sup>‡</sup>
American Chemical Society
2002
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
2002-07-27 00:00:00
Journal contribution
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.