Total Synthesis of (-)-Bastimolide A: A Showcase for Type I Anion Relay Chemistry.

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.

SUBMITTER: Cox JB 

PROVIDER: S-EPMC9256807 | biostudies-literature | 2022 Jul

REPOSITORIES: biostudies-literature