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Issue 42, 2018
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Stereoselective synthesis of E-3-(arylmethylidene)-5-(alkyl/aryl)-2(3H)-furanones by sequential hydroacyloxylation-Mizoroki–Heck reactions of iodoalkynes

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Abstract

A modular, stereoselective synthesis of E-3-(arylidene)-5-(alkyl/aryl)-2(3H)-furanones was developed. The methodology features regioselective addition of β-aryl acrylic acids to iodoacetylenes to furnish the Z-acyloxy iodoalkenes. A stereoselective 5-exo-trig Mizoroki–Heck reaction of the acyloxy iodoalkenes generates the target E-2(3H)-furanones. The approach was applied in a formal synthesis of the naturally occurring kinase inhibitor BE-23372M.

Graphical abstract: Stereoselective synthesis of E-3-(arylmethylidene)-5-(alkyl/aryl)-2(3H)-furanones by sequential hydroacyloxylation-Mizoroki–Heck reactions of iodoalkynes

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Publication details

The article was received on 22 Aug 2018, accepted on 10 Oct 2018 and first published on 10 Oct 2018


Article type: Paper
DOI: 10.1039/C8OB02063A
Citation: Org. Biomol. Chem., 2018,16, 7971-7983
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    Stereoselective synthesis of E-3-(arylmethylidene)-5-(alkyl/aryl)-2(3H)-furanones by sequential hydroacyloxylation-Mizoroki–Heck reactions of iodoalkynes

    G. Muthusamy and S. V. Pansare, Org. Biomol. Chem., 2018, 16, 7971
    DOI: 10.1039/C8OB02063A

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