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On the Verge of Axial Chirality: Atroposelective Synthesis of the AB-Biaryl Fragment of Vancomycin<SUP>,</SUP>
- Source :
- Organic Letters; August 2002, Vol. 4 Issue: 17 p2833-2836, 4p
- Publication Year :
- 2002
-
Abstract
- <UFIGR ID="ol026182en00001">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)-<BO>29</BO>. 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