Stereoselective total synthesis of cananginones (D-I) using Ireland-Claisen rearrangement as a key step

A strategy for stereoselective total synthesis of α-substituted γ-hydroxymethyl γ-butyrolactone containing bioactive natural products cananginones (D-I) has been developed using cheap and commercially available d-mannitol as a chiral pool. The Ireland-Claisen rearrangement is utilized as a key step to generate the α-substituted chiral center of the core lactone moiety, while the elongation of aliphatic side chain by different C-8 hydrocarbon groups have been achieved by alkylation, Cadiot-Chodkiewicz, and Sonogashira reactions.

Graphical abstractDownload full-size imageFirst stereoselective total synthesis of cananginones (D-I) has been accomplished using Ireland-Claisen rearrangement as a key step.