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Expedient Syntheses of β-Iodofurans by 5-endo-dig Cyclisations

✍ Scribed by Sean P. Bew; Gamila M. M. El-Taeb; Simon Jones; David W. Knight; Wen-Fei Tan

Publisher
John Wiley and Sons
Year
2007
Tongue
English
Weight
271 KB
Volume
2007
Category
Article
ISSN
1434-193X

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✦ Synopsis

Abstract

5‐endo‐dig cyclisations of 3‐alkyne‐1,2‐diols using iodine as the electrophile proceed smoothly to deliver excellent yields of the corresponding β‐iodofurans. The necessary precursors are available from a number of different approaches, notably regioselective bis‐hydroxylation of conjugated enynes and the addition of acetylides to α‐hydroxy carbonyl groups. The initial iodofurans can be homologated using a number of strategies, ranging from various transition metal‐catalysed couplings to halogen–metal exchange and subsequent coupling with an electrophile. Hence, this method overall represents a flexible, relatively brief and very efficient approach to a variety of highly substituted furans. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)

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