3 years ago

Diversity-Oriented Synthesis of Spiroannulated Benzofuran-3-one Scaffold of Leptosphaerin C and Congeners via Aryne Insertion

Diversity-Oriented Synthesis of Spiroannulated Benzofuran-3-one Scaffold of Leptosphaerin C and Congeners via Aryne Insertion
Ranjeet A. Dhokale, Santosh B. Mhaske
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.

Publisher URL: http://dx.doi.org/10.1021/acs.joc.7b00606

DOI: 10.1021/acs.joc.7b00606

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