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

doi:10.1039/a700375g

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

Research output: Contribution to journal › Article › peer-review

43 Citations (Scopus)

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 language	English
Pages (from-to)	1819-1824
Number of pages	6
Journal	Journal of the Chemical Society - Perkin Transactions 1
Issue number	12
DOIs	https://doi.org/10.1039/a700375g
Publication status	Published - 21 Jun 1997
Externally published	Yes

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

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.",

author = "Gabbutt, \{Christopher D.\} and Hepworth, \{John D.\} and Urquhart, \{Michael W.J.\} and \{Vazquez De Miguel\}, \{Luis Millan\}",

year = "1997",

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doi = "10.1039/a700375g",

language = "English",

pages = "1819--1824",

journal = "Journal of the Chemical Society - Perkin Transactions 1",

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T1 - Synthesis and conjugate additions of 2,3,4,9-tetrahydro-1H-xanthene-1,9-diones

AU - Gabbutt, Christopher D.

AU - Hepworth, John D.

AU - Urquhart, Michael W.J.

AU - Vazquez De Miguel, Luis Millan

PY - 1997/6/21

Y1 - 1997/6/21

N2 - 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.

AB - 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.

UR - https://www.scopus.com/pages/publications/33748596385

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DO - 10.1039/a700375g

M3 - Article

AN - SCOPUS:33748596385

SN - 0300-922X

SP - 1819

EP - 1824

JO - Journal of the Chemical Society - Perkin Transactions 1

JF - Journal of the Chemical Society - Perkin Transactions 1

IS - 12

ER -

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

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