Synthesis and conjugate additions of 2,3,4,9-tetrahydro-1H-xanthene-1,9-diones

Christopher D. Gabbutt, John D. Hepworth, Michael W.J. Urquhart, Luis Millan Vazquez De Miguel

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Abstract

An efficient two step procedure for the synthesis of 2,3,4,9-tetrahydro-1H-xanthene-1,9-diones is described. A study of their conjugate additions has shown them to be efficient Michael acceptors. Reaction of 2,3,4,9-tetrahydro-1H-xanthene-1,9-dione with tris(methylthio)methyllithium, followed by mercury(II) catalysed methanolysis, gave methyl 1-hydroxy-9-oxo-3,4,4a,9-tetrahydro-2H-xanthene-4a-carboxylate, the nucleus of the secalonic acids and other natural products.

Original languageEnglish
Pages (from-to)1819-1824
Number of pages6
JournalJournal of the Chemical Society - Perkin Transactions 1
Issue number12
DOIs
Publication statusPublished - 21 Jun 1997
Externally publishedYes

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Xanthenes
Biological Products
Mercury

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Gabbutt, Christopher D. ; Hepworth, John D. ; Urquhart, Michael W.J. ; Vazquez De Miguel, Luis Millan. / Synthesis and conjugate additions of 2,3,4,9-tetrahydro-1H-xanthene-1,9-diones. In: Journal of the Chemical Society - Perkin Transactions 1. 1997 ; No. 12. pp. 1819-1824.
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Synthesis and conjugate additions of 2,3,4,9-tetrahydro-1H-xanthene-1,9-diones. / Gabbutt, Christopher D.; Hepworth, John D.; Urquhart, Michael W.J.; Vazquez De Miguel, Luis Millan.

In: Journal of the Chemical Society - Perkin Transactions 1, No. 12, 21.06.1997, p. 1819-1824.

Research output: Contribution to journalArticle

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