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■ Studies on the Biosynthesis of the Stephacidins and Notoamides. Total Synthesis of Notoamides

Timothy J. McAfoos, Shengying Li, Sachiko Tsukamoto, Daivd H. Sherman, and Robert M. Williams*

*Department of Chemistry, Colorado State University, Fort Collins, CO 80523-1872, U.S.A.

Abstract

Notoamide S has been suggested to be the final common precursor between two different Aspergillus sp. fungal strains before diverging to form enantiomerically opposite natural products (+)- and (–)-stephacidin A and (+)- and (-)-notoamide B. The synthesis of notoamide S comes from the coupling of N-Fmoc proline with a 6-hydroxy-7-prenyl-2-reverse prenyl tryptophan derivative that was synthesized via a late stage Claisen rearrangement from a 6-propargyl-2-reverse prenylated indole.