Linear and angular furocoumarins can be obtained starting from phloroglucinol in a versatile, simple, direct, and efficient way, as demonstrated in the divergent syntheses described here. The key step is the alkali-mediated rearrangement of 4-halomethylcoumarins to benzofuran-3-acetic acids via α,β-unsaturated acids and the key intermediates are benzodipyrones, which, depending on their substitution, can either give or fail to give the ring-contraction reaction.
Divergent Synthesis of Linear and Angular Furocoumarin Acetic Acids from Phloroglucinol
DELOGU, GIOVANNA LUCIA;PICCIAU, MARIA CARMEN;
2007-01-01
Abstract
Linear and angular furocoumarins can be obtained starting from phloroglucinol in a versatile, simple, direct, and efficient way, as demonstrated in the divergent syntheses described here. The key step is the alkali-mediated rearrangement of 4-halomethylcoumarins to benzofuran-3-acetic acids via α,β-unsaturated acids and the key intermediates are benzodipyrones, which, depending on their substitution, can either give or fail to give the ring-contraction reaction.
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