Experimental and Computational Studies on Regiodivergent Chiral Phosphoric Acid Catalyzed Cycloisomerization of Mupirocin Methyl Ester.

ABSTRACT: This article presents a new strategy for achieving regiocontrol over the endo versus exo modes of cycloisomerizations of epoxide-containing alcohols, which leads to the formation of five- or six-membered cyclic ethers. Unlike traditional methods relying on achiral reagents or enzymes, this approach utilizes chiral phosphoric acids to catalyze the regiodivergent selective formations of either tetrahydrofuran- or tetrahydropyran-containing products. By using methyl ester of epoxide-containing antibiotic mupirocin as the substrate, it is demonstrated that catalytic chiral phosphoric acids (R)-TCYP and (S)-TIPSY could be used to achieve the selective formation of either the six-membered endo product (95:5 r.r.) or the five-membered exo product (77:23 r.r.), correspondingly. This cyclization wa

SUBMITTER: Wang S 

PROVIDER: S-EPMC7261366 | biostudies-literature | 2020 Apr

REPOSITORIES: biostudies-literature