Synthesis of an Advanced Fragment of (+)-Trienomycinol

Dedicated with great respect to Jean Normant

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.

Key words

ansamycin - trienomycin - antitumor - sulfoxide

• References

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