Synthesis and Bioconversions of Notoamide T: A Biosynthetic Precursor to Stephacidin A and Notoamide B

Abstract

In an effort to further elucidate the biogenesis of the stephacidin and notoamide families of natural products, notoamide T has been identified as the likely precursor to stephacidin A. The total synthesis of notoamide T is described along with it is C-6-epimer, 6-<i>epi</i>-notoamide T. The chemical conversion of stephacidin A to notoamide T by reductive ring opening is described as well as the oxidative conversion of notoamide T to stephacidin A. Furthermore, [¹³C]₂-notoamide T was synthesized and provided to <i>Aspergillus versicolor</i> and <i>Aspergillus</i> sp. MF297-2, in which significant incorporation was observed in the advanced metabolite, notoamide B