Abstract by Alexander Ramos
Chemistry and Biochemistry
Synthesis of Yaku\' Amide Analog EVV
Total synthesis of the anticancer peptide natural product yaku’amide A is reported. Its -tert hydroxy amino acidswere prepared via regioselective aminohydroxylation involving a chiral mesyloxycarbamate reagent. Stereospecificconstruction of the E- and Z-iIle residues was accomplished via a one-pot reaction featuring an anti dehydration, an azidereduction, and an ON acyl transfer. Only negligible amounts of alkene isomerization was observed during this process.These methods enabled a highly convergent synthetic route to the natural product that is amenable to the production of simplified analogues.