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

2012-02-27, Lestini, Elena, Robertson, Keith, Murphy, Cormac D., Paradisi, Francesca

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.