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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-epi-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, [(13)C](2)-notoamide T was synthesized and provided to Aspergillus versicolor and Aspergillus sp. MF297-2, in which significant incorporation was observed in the advanced metabolite, notoamide B.

SUBMITTER: Sunderhaus JD

PROVIDER: S-EPMC3549551 | biostudies-literature | 2013 Jan

REPOSITORIES: biostudies-literature

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Synthesis and bioconversions of notoamide T: a biosynthetic precursor to stephacidin A and notoamide B.

Sunderhaus James D JD McAfoos Timothy J TJ Finefield Jennifer M JM Kato Hikaru H Li Shengying S Tsukamoto Sachiko S Sherman David H DH Williams Robert M RM

Organic letters 20121218 1

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-epi-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, [(13)C](2)-notoamide T was synthesized an ...[more]

PMID: 23249380

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