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

Lestini, ElenaElenaLestiniRobertson, KeithKeithRobertsonMurphy, Cormac D.Cormac D.MurphyParadisi, FrancescaFrancescaParadisi2012-06-122012-06-122012 Taylo2012-02-27Synthetic Communicationshttp://hdl.handle.net/10197/3634Rare 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.244224 bytesapplication/mswordenThis is an electronic version of an article published in Synthetic Communications, available online at: http://dx.doi.org/10.1080/00397911.2011.607936OttelionesDanishefsky’s dieneDiels–Alder cycloaddition4-methylenecyclohex-2-enoneAntineoplastic agentsRing formation (Chemistry)DiolefinsAlternative mild route to the synthesis of 4-methylenecyclohex-2-enone, a key moiety of the anticancer compounds ottelione A and BJournal Article42121864187610.1080/00397911.2011.607936https://creativecommons.org/licenses/by-nc-sa/1.0/