Article ID | Journal | Published Year | Pages | File Type |
---|---|---|---|---|
5216714 | Tetrahedron | 2014 | 14 Pages |
Abstract
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.
Keywords
Related Topics
Physical Sciences and Engineering
Chemistry
Organic Chemistry
Authors
Tapan Kumar Kuilya, Shamba Chatterjee, Rajib Kumar Goswami,