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1. On the verge of axial chirality: atroposelective synthesis of the AB-biaryl fragment of vancomycin.

Author

Bringmann G, Menche D, Mühlbacher J, Reichert M, Saito N, Pfeiffer SS, and Lipshutz BH

Subjects
Chlorine, Lactones chemistry, Models, Molecular, Molecular Conformation, Stereoisomerism, Anti-Bacterial Agents chemical synthesis, Vancomycin chemical synthesis
Abstract

[structure: see text] 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)-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.

Published
2002
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