Diversity-Oriented Synthesis of Spiroannulated Benzofuran-3-one Scaffold of Leptosphaerin C and Congeners via Aryne Insertion.
Ranjeet A DhokaleSantosh B MhaskePublished in: The Journal of organic chemistry (2017)
A concise synthesis of functionalized cyclohexenone-fused spirobenzofuran-3-ones under mild reaction conditions was developed. The reaction proceeds via insertion of aryne into the C-O bond followed by a regioselective intramolecular conjugate addition. The use of silyl-protected acid was crucial for the transformation. This protocol was successfully applied for the synthesis of leptosphaerin C core and its novel analogues.