title: Synthetic strategies to epoxydiynes and a key synthon of the neocarzinostatin chromophore.
abstract: We present herein our recent efforts towards the synthesis of epoxydiynes which represent an unusual structural feature of the neocarzinostatin chromophore. A number of different routes to these epoxydiynes have been explored with varying success. Ultimately a concise and convergent approach was developed, which involved the addition of an allenyl zinc bromide to propargylic ketones/aldehydes followed by epoxide formation. This new protocol enabled us to synthesise a fully elaborated epoxydiyne which will find application for our studies towards the total synthesis of the NCS chromophore.
authors.affiliation: Department of Chemistry, University College London, 20 Gordon Street, London, UK.
authors.forename: Olivier
authors.initials: O
authors.lastname: Thominet
authors.forename: James R
authors.initials: JR
authors.lastname: Baker
authors.forename: Hugh
authors.initials: H
authors.lastname: Britton
authors.forename: Zac C
authors.initials: ZC
authors.lastname: Etheridge
authors.forename: Marco G
authors.initials: MG
authors.lastname: Soscia
authors.forename: Stephen
authors.initials: S
authors.lastname: Caddick
mesh_terms: D003890:Desiccation; D053281:Enediynes / Q000737:chemistry*; D004852:Epoxy Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D004952:Esters / Q000138:chemical synthesis; D007659:Ketones / Q000737:chemistry; D008956:Models, Chemical; D013237:Stereoisomerism; D009353:Zinostatin / Q000031:analogs & derivatives / Q000737:chemistry
chemical_list: D053281:Enediynes; D004852:Epoxy Compounds; D004952:Esters; D007659:Ketones; C032372:neocarzinostatin chromophore; D009353:Zinostatin