Studies on the Biosynthesis of Chetomin: Enantiospecific Synthesis of a Putative, Late-Stage Biosynthetic Intermediate.
The enantiospecific synthesis of desthiochetomin, a putative biosynthetic intermediate of the epidithiodioxopiperazine natural product chetomin, is described. A diastereoselectiveN-alkylation was employed to form the key C3-N1' bond of the heterodimeric indoline core, followed by peptide coupling and dioxopiperazine cyclization with the requisiteN-methyl amino acids. A related sarcosine-derived dioxopiperazine was prepared in the same manner. The first proposed biosynthesis of chetomin is also detailed in the text.
Department of Chemistry, Colorado State University, Fort Collins, CO 80523, USA.
Timothy R
TR
Welch
Department of Chemistry, Colorado State University, Fort Collins, CO 80523, USA ; University of Colorado Cancer Center, Aurora, CO 80045, USA.
Robert M
RM
Williams
Aspergillus versicolor; biosynthesis; prenylated indole alkaloid