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

…, D Menche, J Mühlbacher, M Reichert, N Saito…

Index: Bringmann, Gerhard; Menche, Dirk; Muehlbacher, Joerg; Reichert, Matthias; Saito, Nozomi; Pfeiffer, Steven S.; Lipshutz, Bruce H. Organic Letters, 2002 , vol. 4, # 17 p. 2833 - 2836

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Citation Number: 32

Abstract

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 ...