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

ABSTRACT: 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 (12α , β) 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. Under the same reaction conditions, xanthate derived from the β-furanose isomer affords a high yield of deoxygenated product, whereas the α-isomer produces a very low yield. The key transformations used were Wittig olefination, TEMPO mediated oxidation, and Barton-McCombie deoxygenation, resul

SUBMITTER: Desireddi JR 

PROVIDER: S-EPMC9449999 | biostudies-literature | 2022 Sep

REPOSITORIES: biostudies-literature