Alternative mild route to the synthesis of 4-methylenecyclohex-2-enone, a key moiety of the anticancer compounds ottelione A and B

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Title: Alternative mild route to the synthesis of 4-methylenecyclohex-2-enone, a key moiety of the anticancer compounds ottelione A and B
Authors: Lestini, Elena
Robertson, Keith
Murphy, Cormac D.
Paradisi, Francesca
Permanent link: http://hdl.handle.net/10197/3634
Date: 27-Feb-2012
Abstract: Rare 4-methylenecyclohex-2-enone is prepared from a Diels-Alder methanesulfonate adduct and sodium iodide in acetone in up to 70% yield under mild conditions. This procedure is envisaged to be relevant to the synthesis of 4-methylenecyclo hex-2-enone analogues, structurally similar to the key functionality of cytotoxic otteliones and with potentially significant bioactivity.
Funding Details: Higher Education Authority
Type of material: Journal Article
Publisher: Taylor & Francis
Journal: Synthetic Communications
Volume: 42
Issue: 12
Start page: 1864
End page: 1876
Copyright (published version): 2012 Taylor & Francis
Keywords: OttelionesDanishefsky’s dieneDiels–Alder cycloaddition4-methylenecyclohex-2-enone
Subject LCSH: Antineoplastic agents
Ring formation (Chemistry)
Diolefins
DOI: 10.1080/00397911.2011.607936
Language: en
Status of Item: Peer reviewed
Appears in Collections:Chemistry Research Collection

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