Lakehead University Library Logo
    • Login
    View Item 
    •   Knowledge Commons
    • Electronic Theses and Dissertations
    • Retrospective theses
    • View Item
    •   Knowledge Commons
    • Electronic Theses and Dissertations
    • Retrospective theses
    • View Item
    JavaScript is disabled for your browser. Some features of this site may not work without it.
    quick search

    Browse

    All of Knowledge CommonsCommunities & CollectionsBy Issue DateAuthorTitleSubjectDisciplineAdvisorCommittee MemberThis CollectionBy Issue DateAuthorTitleSubjectDisciplineAdvisorCommittee Member

    My Account

    Login

    Statistics

    View Usage Statistics

    Synthetic studies on chaksine

    Thumbnail

    View/Open

    MiahM1981m-1b.pdf (41.87Mb)

    Date

    1981

    Author

    Miah, M. A. J.

    Degree

    Master of Science

    Discipline

    Chemistry

    Subject

    Chaksine.

    Metadata

    Show full item record

    Abstract

    This thesis is concerned with the studies in the synthesis of a monoterpenoid alkaloid, chaksine. Ethyl 2-n~butyl-4-bromoacetoacetate (11) was treated with sodium azide to give ethyl 2-n-butyl-4-azidoacetoacetate (12), Catalytic hydrogenation of (12) in presence of hydrochloric acid followed by the reaction of the hydrogenation product (13) with potassium cyanate afforded 4-(1'- carbethoxypenty1)-2-imidazolone (14) or 4-(1'-carboxypentyl)- 2-imidazolone (15) depending on reaction condition. 4-(1'-carbethoxymethyl)-2-imidazolone (25) was also prepared starting from ethyl 4-bromoacetoacetate (23a) following the same series of reaction as described for the compound (14). Ethyl 2-[4'-methy1-5'-(2"-tetrahydropyranyloxy1)pentyl] acetoacetate (20) was prepared from the reaction of ethyl acetoacetate and 5-bromo-2-methyl-1-(2'-tetrahydropyranyloxyl)pentane (19). Removal of the 3,4- dihydropyran protecting group from (20) yielded ethyl 2-(4'-methyl—5'-hydroxypentyl)acetoacetate (21). The compound (21) was also prepared directly by the reaction of ethylacetoacetate with 5-bromo-2-methyl- pentanol (18), The compound (21) was then subjected to bromination to give (22a) followed by the treatment of (22a) with sodium azide to yield ethyl 2-(4'-methyl-5'-hydroxypentyl)-4-azidoacetoacetate (22b) .

    URI

    http://knowledgecommons.lakeheadu.ca/handle/2453/2371

    Collections

    • Retrospective theses

    Lakehead University Library
    Contact Us | Send Feedback

     


    Lakehead University Library
    Contact Us | Send Feedback