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 dev...

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Bibliographic Details
Published inOrganic & biomolecular chemistry Vol. 5; no. 22; pp. 3703 - 3712
Main Authors Thominet, Olivier, Baker, James R., Britton, Hugh, Etheridge, Zac C., Sosciab, Marco G., Caddick, Stephen
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 01.01.2007
Subjects
Chemistry
Chemistry, Organic
Desiccation
Enediynes - chemistry
Epoxy Compounds - chemical synthesis
Epoxy Compounds - chemistry
Esters - chemical synthesis
Ketones - chemistry
Models, Chemical
Physical Sciences
Science & Technology
Stereoisomerism
Zinostatin - analogs & derivatives
Zinostatin - chemistry
SECONDARY ALCOHOLS
REARRANGEMENT
CORE
ROUTE
KEDARCIDIN
ACTIVATION
STEREOSELECTIVE-SYNTHESIS
ADDITIONS
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Summary: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.
ISSN:1477-0520
1477-0539
DOI:10.1039/b711196g