Gold-catalyzed endo-selective Ring-opening of Epoxides and its Application in Construction of Poly-ethers.

Abstract

Tetrahydropyran and tetrahydropyran-fused poly-ethers scaffolds are found in many classes of natural products and medicinally relevant small molecules. Here we describe a catalytic system for 6-endo selective ring-opening of epoxides by Au(I) or Au(III) catalyst that provides rapid access to various tetrahydropyran-derived motifs. It also could efficiently construct the subunits of marine ladder-like poly-ethers through emulating the Nakanishi's hypothesis on the biosynthesis of these toxins. The synthetic utility of this method is also demonstrated in the preparation of the tricyclic core of tetrahydropyran-containing macrolide natural products lituarines A-C.