The concept of non-conjugated-to-conjugated double bond isomerization as a triggering mechanism for a calicheamicin model was tested. A bicyclo[7.3.1] enediyne framework was prepared with a bridgehead double bond and an acetonyl side chain. Base-promoted exchange failed to produce the conjugated isomer. Computational analysis suggested that additional conjugating groups would favor the isomerization, but experiment proved that not to be correct.
All Science Journal Classification (ASJC) codes
- Drug Discovery
- Organic Chemistry
- Alkene isomerization
- Enol-keto isomerization