Synthesis of an Advanced Fragment of (+)-Trienomycinol

Abstract

The synthesis of the fully functionalized eastern fragment of trienomycins A–F, ansamycin antibiotics is described. A key step involves a peptidic coupling between a sulfonyl aniline and an enantiopure carboxylic acid obtained by a completely diastereoselective reduction of a β-ketosulfoxide to generate the stereogenic carbinol. Studies on the coupling with the western part were also performed, giving access to an advanced fragment of trienomycinol.