Kinetic analysis of a reactive model enediyne

M. F. Semmelhack, R. Sarpong

Research output: Contribution to journalArticlepeer-review

8 Scopus citations

Abstract

A model framework related to the calcheamicin family of enediyne toxins was evaluated in its reactivity toward cycloaromatization through the arene 1,4-diyl intermediates and hydrogen atom abstractions. The keto version 9 is relatively unreactive, with t1/2 = 1.5 h at 60°C. The product from hydride reduction of the ketone, alcohol 13b, is much more reactive, with t1/2 = 50 min at 0°C. In both cases, the rate of rearrangement is independent of the hydrogen atom donor, consistent with a rate-determining first step (cyclization).

Original languageEnglish (US)
Pages (from-to)807-813
Number of pages7
JournalJournal of Physical Organic Chemistry
Volume17
Issue number9
DOIs
StatePublished - Sep 1 2004

All Science Journal Classification (ASJC) codes

  • Physical and Theoretical Chemistry
  • Organic Chemistry

Keywords

  • Arene diradical
  • Calicheamicin
  • Enediyne model
  • Hydrogen atom abstraction

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