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    Synthetic studies on slaframine

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    RahmanM1980m-1b.pdf (17.69Mb)

    Date

    1980

    Author

    Rahman, M. A.

    Degree

    Master of Science

    Discipline

    Chemistry

    Subject

    Slaframine

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    Abstract

    Thjs thesis is concerned with the prelIminary studies in the synthesis of an indolizine alkaloid, slaframine. A Wittig reaction of 3-carbethoxypropyltriphenylphosophonium iodide (43) with 4-pentenal (44) gave ethyl-(Z)-4,8-nonadienoate (45). Hydrolysis of this product gave the unsaturated acid (46) which was then converted into acid chloride (47), acylazide (48), isocyanate (49) and finally l-amino-3,7-octadiene (50) . The primary amino group of (50) was protected by forming trifluoroacetate derivative (51). 1- Amino-3,7-octadiene was converted in N-(Benzyloxycarbonyl)-3,7-octadiene (52) which was finally converted into epoxide (53). Other related studies involved: (1) preparation of 1,2-oxidocyclohex-4-ene (54) which was converted into trans-2-azidocyclohex-4-enol (55). The secondary alcohol group was protected by forming acetate derivative (56). A tetrahydropyranyl derivative (57) was also prepared.

    URI

    http://knowledgecommons.lakeheadu.ca/handle/2453/2405

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