Synthetic strategies to epoxydiynes and a key synthon of the neocarzinostatin chromophore.
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.
Thominet
Olivier
O
Department of Chemistry, University College London, 20 Gordon Street, London, UK.
Baker
James R
JR
Britton
Hugh
H
Etheridge
Zac C
ZC
Soscia
Marco G
MG
Caddick
Stephen
S
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
D053281:Enediynes; D004852:Epoxy Compounds; D004952:Esters; D007659:Ketones; C032372:neocarzinostatin chromophore; D009353:Zinostatin