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

Abstract

Herein, we described the novel synthetic strategy for the total synthesis of harvestmen natural product (4S,5S)‑4-hydroxy-γ-decalactone (minor) from an inexpensive precursor ((R)-2,2-dimethyl-1,3-dioxolane-4-carbaldehyde) with 31% overall yield. Hydroxy-γ-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.