Total Synthesis and Structure Revision of a Fungal Glycolipid Fusaroside

Herein, we report a strategy for the total synthesis of a structurally unique fungal glycolipid fusaroside. The first total synthesis of the proposed structure involved construction of the complex, branched lipid chain having a variety of alkenes with E stereochemistry and attachment of the masked alpha,beta-unsaturated beta-keto acid at the O-4 position of trehalose as key steps. We propose a revision in the structure of fusaroside, particularly the position of olefins in the lipid chain.

Automated summary

In this study, a total synthesis strategy for the structurally unique fungal glycolipid fusaroside was reported, with a proposed revision in its structure, particularly regarding the position of olefins in the lipid chain.