An arene-alkene photocycloaddition-radical cyclization cascade

The first synthesis of cis,cis,cis,trans-[5.5.5.5]-fenestranes

Paul A. Wender, Timothy Dore, Mitch A. DeLong

    Research output: Contribution to journalArticle

    Abstract

    The first cis,cis,cis,trans-[5.5.5.5]-fenestranes have been synthesized in three steps using a novel arene-alkene photocycloaddition-radical cyclization cascade, which creates overall 5 new rings and 8 stereogenic centers. A lead tetraacetate mediated ring expansion of a 5,5-fused ring system, discovered in the course of exploring the chemistry of these new materials, is also described.

    Original languageEnglish (US)
    Pages (from-to)7687-7690
    Number of pages4
    JournalTetrahedron Letters
    Volume37
    Issue number43
    DOIs
    StatePublished - Oct 21 1996

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    Cyclization
    Alkenes
    lead tetraacetate

    ASJC Scopus subject areas

    • Biochemistry
    • Drug Discovery
    • Organic Chemistry

    Cite this

    An arene-alkene photocycloaddition-radical cyclization cascade : The first synthesis of cis,cis,cis,trans-[5.5.5.5]-fenestranes. / Wender, Paul A.; Dore, Timothy; DeLong, Mitch A.

    In: Tetrahedron Letters, Vol. 37, No. 43, 21.10.1996, p. 7687-7690.

    Research output: Contribution to journalArticle

    Wender, Paul A. ; Dore, Timothy ; DeLong, Mitch A. / An arene-alkene photocycloaddition-radical cyclization cascade : The first synthesis of cis,cis,cis,trans-[5.5.5.5]-fenestranes. In: Tetrahedron Letters. 1996 ; Vol. 37, No. 43. pp. 7687-7690.
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