Rice Univesrity Logo
    • FAQ
    • Deposit your work
    • Login
    View Item 
    •   Rice Scholarship Home
    • Rice University Graduate Electronic Theses and Dissertations
    • Rice University Electronic Theses and Dissertations
    • View Item
    •   Rice Scholarship Home
    • Rice University Graduate Electronic Theses and Dissertations
    • Rice University Electronic Theses and Dissertations
    • View Item
    JavaScript is disabled for your browser. Some features of this site may not work without it.

    Studies in terpene synthesis: a model investigation

    Thumbnail
    Name:
    RICE0065.pdf
    Size:
    1.274Mb
    Format:
    PDF
    View/Open
    Author
    Guin, Henry Wayne
    Date
    1964
    Advisor
    Turner, Richard B.
    Degree
    Master of Arts
    Abstract
    In an attempt to find a feasible synthetic route to the C/D ring system in the terpene kaurene and the terpene alkaloids veatchine and garryine a model synthesis was undertaken. The benzal derivative (1) of 1-hydrindanone on alkylation with methallyl iodide gave (2). The stereochemistry of the ring fusion of (2) was not established, but may be considered to be cis by analogy to similar alkylations. Ozonolysis of (2) gave (3) having carbonyl bands at 5.55, 5.70, and 5.83p. (methylene chloride). Compound (3) was considered to be the anhydride, rather than the expected triketone, on the basis of elemental analysis; and a concerted mechanism, involving the ozonide I, was proposed to account for its formation; and on basic hydrolysis of (3) compound (4), having infrared absorption not unlike that of a diacid, was obtained. Lithium aluminum hydride reduction of (2) gave (5), which formed the acetoxy derivative (6). Ozonolysis of (6) gave (7), which was converted to the diketo alcohol (8) by basic hydrolysis. Compound (8) was converted to the acetate (9), which was considered to be an isomer of (7) by mixed melting point depression, since the infrared spectra of (7) and (9) were identical. More work needs to be done to establish the configuration of (7) and (9). Yields in the reactions were not high enough to merit application of the method in the synthesis of the terpenes considered.
    Citation
    Guin, Henry Wayne. "Studies in terpene synthesis: a model investigation." (1964) Master’s Thesis, Rice University. https://hdl.handle.net/1911/89030.
    Metadata
    Show full item record
    Collections
    • Rice University Electronic Theses and Dissertations [13409]

    Home | FAQ | Contact Us | Privacy Notice | Accessibility Statement
    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
    Site Map

     

    Searching scope

    Browse

    Entire ArchiveCommunities & CollectionsBy Issue DateAuthorsTitlesSubjectsTypeThis CollectionBy Issue DateAuthorsTitlesSubjectsType

    My Account

    Login

    Statistics

    View Usage Statistics

    Home | FAQ | Contact Us | Privacy Notice | Accessibility Statement
    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
    Site Map