Gold‐catalyzed endo‐selective Ring‐opening of Epoxides and its Application in Construction of Poly‐ethers.
- Resource Type
- Article
- Authors
- Wu, Kehuan; Kang, Kaiwen; Liu, Dan; Zhang, Chiyue; Wang, Xinyu; Zhang, Miaocheng; Li, Qi
- Source
- Chemistry - A European Journal. 4/11/2024, Vol. 30 Issue 21, p1-9. 9p.
- Subject
- *EPOXY compounds
*SMALL molecules
*NATURAL products
*MARINE toxins
*BIOSYNTHESIS
*TOXINS
- Language
- ISSN
- 0947-6539
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. [ABSTRACT FROM AUTHOR]