A highly convergent and enantiospecific synthesis of acyclic subunits of ionomycin from a single chiral progenitor

Abstract

The C2–C10 and C11–C22 subunits of ionomycin were synthesized from a chiron derived from L-glutamic acid or D-ribonolactone. A strategy is presented in which C-methyl and hydroxyl groups are introduced on appropriate carbon frameworks in a completely predictable fashion based on the replicating lactone method, thus chemically matching any substitution pattern arising from the propionate biosynthetic pathway.