Oxa-enediynes: Probing the electronic and stereoelectronic contributions to the bergman cycloaromatization

Graham B. Jones, Justin M. Wright, George Hynd, Justin K. Wyatt, Philip M. Warner, Robert S. Huber, Aiwen Li, Michael W. Kilgore, Robert P. Sticca, Richard S. Pollenz

Research output: Contribution to journalArticlepeer-review

36 Scopus citations

Abstract

Efficient routes to three classes of 10-membered oxa-enediynes are presented. The electronic and stereoelectronic contributions to half-lives are supported by density functional theory calculations. One member of this class cyclizes to give an isochroman which binds to and degrades the aryl hydrocarbon receptor (AhR).

Original languageEnglish
Pages (from-to)5727-5732
Number of pages6
JournalJournal of Organic Chemistry
Volume67
Issue number16
DOIs
StatePublished - Aug 9 2002

Funding

FundersFunder number
National Institute of General Medical SciencesR01GM057123

    ASJC Scopus subject areas

    • Organic Chemistry

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