Total Synthesis of (−)‐Bastimolide A: A Showcase for Type I Anion Relay Chemistry
Joshua B. Cox, Alex Kellum, Yiwen Zhang, Bo Li, Amos B. Smith
Abstract
A 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.
Topics & Concepts
RelayIonChemistryPhysicsOrganic chemistryQuantum mechanicsPower (physics)Synthetic Organic Chemistry MethodsChemical synthesis and alkaloidsAsymmetric Synthesis and Catalysis