Evaluation of alkene isomerization as a trigger for enediyne activation

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

Research output: Contribution to journalArticlepeer-review

6 Scopus citations

Abstract

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
Volume43
Issue number4
DOIs
StatePublished - Jan 21 2002

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Fingerprint Dive into the research topics of 'Evaluation of alkene isomerization as a trigger for enediyne activation'. Together they form a unique fingerprint.

Cite this