NMR data of multi-step synthesis of (R)-3-hydroxy-fatty acid derivatives from levoglucosenone

Résumé 0

This dataset archives NMR data related to synthesis of (R)-3-hydroxydecanoic acid and analogues. These data have been produced during LéGO project which aimed to green up the synthetic pathway of rhamnolipids. Exhibiting outstanding biosurfactant properties, rhamnolipids (RLs) are highly valuable molecules in the cosmetic, pharmaceutic and agricultural sectors. In the latter, they are used to artificially stimulate natural immune system of crops (also known as elicitation). To decipher their mechanisms of action and design novel potent elicitors, a straightforward and green access to model molecules is needed. Herein, starting from cellulose-derived levoglucosenone, we propose an efficient and seven-step synthetic pathway to prepare enantiopure (R)-3-hydroxy-fatty acid chains present in RLs with Michael addition, Baeyer-Villiger oxidation, Bernet-Vasella reaction and cross metathesis homologation as key steps (global yield ranging from 24% to 36%).