Stereoselective total synthesis of arachnid harvestmen natural product: (4S,5S)-4-hydroxy-γ-decalactone

Herein, we described the novel synthetic strategy for the total synthesis of harvestmen natural product (4S,5S)-4-hydroxy-gamma-decalactone (minor) from an inexpensive precursor ((R)-2,2-dimethyl-1,3-dioxolane-4-carbaldehyde) with 31% overall yield. Hydroxyy-lactones represent a special class of harvestmen exocrine defense compounds. The present convergent synthesis utilizes classical reactions like the Barbier reaction, the Grignard reaction, and the employment of an olefin as a masked carboxylic acid functionality followed by lactone formation as key steps.

Automated summary

In this study, we described a novel synthetic strategy for the total synthesis of the harvestmen natural product (4S,5S)-4-hydroxy-gamma-decalactone (minor) using an inexpensive precursor. The synthesis achieved an overall yield of 31% and utilized classical reactions and key steps involving olefin and lactone formation.