Concise Stereoselective Synthesis of β-Hydroxy-γ-lactones: (4,5)-4-Hydroxy-γ-decalactone from the Japanese Orange Fly and Enantiomers of Arachnid Harvestmen Isolates.

The naturally occurring (4,5)-4-hydroxy-γ-decalactone from the Japanese orange fly and the antipode of (4,5)-4-hydroxy-γ-dodecalactone from the harvestmen arachnid and their stereoisomers are synthesized from the chiral pool material d-glucono-δ-lactone in a few steps. The one-pot conversion of the latter to γ-vinyl-β-hydroxy-γ-lactone, cross-metathesis with requisite olefin, and hydrogenation enabled the synthesis of -lactones in just a two-pot operation. An additional efficient Pd-catalyzed allylic isomerization of γ-vinyl-β-hydroxy-γ-lactone led to the -lactones in high yields.