Evaluation of alkene isomerization as a trigger for enediyne activation

M. F. Semmelhack, Richmond Sarpong, Jeffrey Bergman, Douglas M. Ho

Research output: Contribution to journalArticlepeer-review

8 Scopus citations


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.

Original languageEnglish (US)
Pages (from-to)541-544
Number of pages4
JournalTetrahedron Letters
Issue number4
StatePublished - Jan 21 2002

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry


  • Alkene isomerization
  • Enediynes
  • Enol-keto isomerization


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