An efficient synthesis of epoxydiynes and a key fragment of neocarzinostatin chromophore.
[reaction: see text] A key structural feature of the Neocarzinostatin chromophore is a reactive epoxydiyne. We present here a new method for the preparation of epoxydiynes by the addition of an allenyl zinc bromide to a propargylic ketone.
Baker
J R
JR
Department of Chemistry, Christopher Ingold Laboratories, University College London, 20 Gordon Street, London WC1H OAJ, United Kingdom.
Thominet
O
O
Britton
H
H
Caddick
S
S
D001965:Bromides / Q000737:chemistry; D053281:Enediynes / Q000138:chemical synthesis* / Q000737:chemistry; D004852:Epoxy Compounds / Q000138:chemical synthesis / Q000737:chemistry*; D007659:Ketones / Q000737:chemistry; D008956:Models, Chemical; D015394:Molecular Structure; D013237:Stereoisomerism; D013302:Streptomyces / Q000737:chemistry; D017967:Zinc Compounds / Q000737:chemistry; D009353:Zinostatin / Q000031:analogs & derivatives / Q000138:chemical synthesis / Q000737:chemistry
D001965:Bromides; D053281:Enediynes; D004852:Epoxy Compounds; D007659:Ketones; D017967:Zinc Compounds; C032372:neocarzinostatin chromophore; D009353:Zinostatin; C093802:zinc bromide