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    AN APPROACH TO THE SYNTHESIS OF STIPITATIC ACID

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    Author
    MAUPIN, PAUL HUTSELL, II
    Date
    1983
    Degree
    Doctor of Philosophy
    Abstract
    An approach to the synthesis of the penicilium mold metabolite stipitatic acid has been investigated. It involved the preparation of a bis-(alpha)-diazoketone derived from citric acid, whose central (alpha)-hydroxy acid function had been masked and protected, and its conversion into a 6,6-disubstituted 2-cycloheptene-1,4-dione by intramolecular diazoketone coupling catalyzed by bis-cyclopentadienylnickel (nickelocene). Bromination of the enedione, followed by dehydrobromination, yielded a bromoenedione. (beta)-Elimination of both enediones with potassium hydroxide gave (gamma)-tropolones. Alakali treatment of the bromotropolone afforded a phenolic ring contraction product.
    Keyword
    Organic chemistry
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    Managed by the Digital Scholarship Services at Fondren Library, Rice University
    Physical Address: 6100 Main Street, Houston, Texas 77005
    Mailing Address: MS-44, P.O.BOX 1892, Houston, Texas 77251-1892