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On the Verge of Axial Chirality:  Atroposelective Synthesis of the AB-Biaryl Fragment of Vancomycin<SUP>,</SUP>

Authors :
Bringmann, G.
Menche, D.
Muhlbacher, J.
Reichert, M.
Saito, N.
Pfeiffer, S. S.
Lipshutz, B. H.
Source :
Organic Letters; August 2002, Vol. 4 Issue: 17 p2833-2836, 4p
Publication Year :
2002

Abstract

&lt;UFIGR ID=&quot;ol026182en00001&quot;&gt;Using 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)-&lt;BO&gt;29&lt;/BO&gt;. 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.

Details

Language :
English
ISSN :
15237060 and 15237052
Volume :
4
Issue :
17
Database :
Supplemental Index
Journal :
Organic Letters
Publication Type :
Periodical
Accession number :
ejs3634466
Full Text :
https://doi.org/10.1021/ol026182e