Tetrahedron Letters

A general route to 5-substituted-2-furylacetic acids: a brief synthesis of plakorsin B

SJ Hayes, DW Knight, AWT Smith, MJ O'Halloran

Index: Hayes, Simon J.; Knight, David W.; Smith, Andrew W.T.; O'Halloran, Mark J. Tetrahedron Letters, 2010 , vol. 51, # 4 p. 717 - 719

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Citation Number: 4

Abstract

3, 4-Dihydroxy-5-alkynylcarboxylic acids, readily obtained by the addition of lithium acetylides to α-acetoxysuccinic anhydride followed by reduction and hydrolysis, undergo smooth silver (I)-catalysed 5-endo-dig cyclisations and in situ dehydration to give excellent overall yields of 5-substituted-2-furylacetic acids, including the natural metabolite plakorsin B.