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J Org Chem. 2013 Apr 5;78(7):3464-9. doi: 10.1021/jo400099x. Epub 2013 Feb 27.

Synthesis of 4-vinylindoles using ruthenium-catalyzed ring-closing enyne metathesis.

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  • 1Department of Chemistry, Graduate School of Science, Chiba University, Yayoi-cho, Inage-ku, Chiba 263-8522, Japan.


The selective synthesis of substituted 4-vinylindoles by the ring-closing enyne metathesis (RCEM)/dehydration sequence is reported. In contrast with many known methods in which a pyrrole ring is constructed onto a functionalized benzene precursor, this method enables the construction of a benzene ring onto a pyrrole precursor. The RCEM/tautomerization sequence for the synthesis of 7-hydroxy-4-vinylindole is also presented as an application of this method.

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