Efficient Synthesis of Fused Polycyclic Ether Systems via Sulfonium Ylides: A Synthetic Approach to Yessotoxin and Adriatoxin
Federico Moya-Utrera, Iván Cheng-Sánchez, Irama Fuentes-Pino, Antonio Sánchez-Ruiz, Francisco Sarabia
TL;DR
Researchers developed a new method to create complex ring structures found in marine toxins using chiral sulfonium salts.
Contribution
A novel diastereoselective synthesis approach using chiral sulfonium salts for fused polycyclic ether systems.
Findings
Chiral sulfonium salts from L- and D-methionine enabled diastereoselective epoxy amide synthesis.
The method was applied to construct the tricyclic A–C system in yessotoxin and adriatoxin.
The approach is applicable to various marine-derived fused polycyclic ether toxins.
Abstract
A novel class of chiral sulfonium salts, derived from L- and D-methionine, was designed and successfully employed for the diastereoselective synthesis of epoxy amides. This new methodology of asymmetric epoxidation was exploited for the stereoselective construction of fused polycyclic ethers, which are structural motifs present in a great variety of natural products of marine origin. This methodology proved to be useful for the synthesis of the tricyclic A–C system contained in yessotoxin and adriatoxin, and also in many other related natural products of marine origin belonging to the fused polycyclic ether toxins.
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Taxonomy
TopicsMarine Toxins and Detection Methods · Synthetic Organic Chemistry Methods · Synthesis and Catalytic Reactions