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A convenient synthesis of naturally occurring benzofuran ailanthoidol

โœ Scribed by Chai-Lin Kao; Ji-Wang Chern


Publisher
Elsevier Science
Year
2001
Tongue
French
Weight
86 KB
Volume
42
Category
Article
ISSN
0040-4039

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โœฆ Synopsis


A convenient method for the synthesis of ailanthoidol starting from vanillin is provided using trimethylsilyldiazomethane lithium salt to generate a diphenylacetylene and subsequent oxymercuration cyclization of the resulting alkyne with mercury acetate in acetic acid as key steps.


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A general method of synthesis of 2-aryl-7-alkoxy-benzofurans is described using a benzoannulation reaction as key step. The usefulness of this approach is shown in the new synthesis of ailanthoidol, a benzofuranoid neolignan isolated from the tree Zanthoxylum ailanthoides.