BYU

Abstract by Alexander Ramos

Personal Infomation


Presenter's Name

Alexander Ramos

Degree Level

Doctorate

Abstract Infomation


Department

Chemistry and Biochemistry

Faculty Advisor

Steven Castle

Title

Synthesis of Yaku\' Amide Analog EVV

Abstract

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 ON 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.