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

✍ Scribed by Simon J. Hayes; David W. Knight; Andrew W.T. Smith; Mark J. O’Halloran

Publisher: Elsevier Science
Year: 2010
Tongue: French
Weight: 278 KB
Volume: 51
Category: Article
ISSN: 0040-4039
DOI: 10.1016/j.tetlet.2009.11.120

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✦ Synopsis

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

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