Study of the β-oxygen effect in the Barton-McCombie reaction for the total synthesis of (4,5)-4-hydroxy-γ-decalactone (Japanese orange fly lactone): a carbohydrate based approach.

Efficient and facile synthesis of Japanese orange fly lactone (1) was achieved from a commercially available d-glucose by investigating the Barton-McCombie reaction with furanose anomeric isomers ( , ) with an overall yield of 12.6%. During the course of this synthesis, the β-oxygen effect was discovered in the deoxygenation step at the C-3 position using the Barton-McCombie reaction, where the substrate allows the effect to operate in one of the isomers but not in the other.