Total Synthesis of (−)‐Bastimolide A: A Showcase for Type I Anion Relay Chemistry

Abstract

AbstractA highly convergent total synthesis of (−)‐bastimolide A (1), a polyhydroxy antimalarial macrolide, has been achieved via a longest linear sequence of twenty steps from commercially available glycidyl ethers. Type I Anion Relay Chemistry (ARC) coupling tactics enable rapid construction of the molecule's 1,5‐polylol backbone. A late‐stage B‐alkyl Suzuki–Miyaura union and an Evans‐modified Mukaiyama macrolactonization generate the forty‐membered Z‐α,β‐unsaturated macrocyclic lactone.