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Efficient and Stereoselective Access to the Polyol Fragment C9−C16 of Ansamycin Antibiotics

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posted on 2009-08-20, 00:00 authored by Michel Obringer, Marie Barbarotto, Sabine Choppin, Françoise Colobert
Efficient synthesis of the fragment C9−C16 bearing the anti,syn stereotriad of ansamycin antibiotics is described. Key steps for controlling the configuration of the three stereogenic centers involve a stereoselective Reformatsky-type reaction followed by a diastereoselective reduction of a β-ketosulfoxide.