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    Approaches to the synthesis of dolastatin 11.

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    Author
    Gangwar, Sanjeev.
    Issue Date
    1992
    Keywords
    Dissertations, Academic.
    Chemistry, Organic.
    Committee Chair
    Bates, Robert B.
    
    Metadata
    Show full item record
    Publisher
    The University of Arizona.
    Rights
    Copyright © is held by the author. Digital access to this material is made possible by the University Libraries, University of Arizona. Further transmission, reproduction or presentation (such as public display or performance) of protected items is prohibited except with permission of the author.
    Abstract
    A synthetic route to a stereoisomer of dolastatin 11, a potent antineoplastic agent from the sea hare Dolabella auricularia, is explored. Synthons for the three unusual acids were prepared as follows: (1) Hmp was prepared by a reaction used previously, but the yield was doubled and the isolation procedure greatly simplified. (2) An indirect procedure was developed for putting in the Ibu unit, with the gem-dimethyls added later. (3) Asymmetric syntheses of two Map stereoisomers established the two configurations in this unit in dolastatin 11 and in the related substances dolastatin 12, majusculamide C and 57-normajusculamide C. The nine pieces required for the 3R, 4S, 12S-stereoisomer of dolastatin 11 were assembled in a convergent synthesis to give a product which probably contains a stereoisomer of 1. An analogous route starting from the correct Map stereoisomer will very likely yield dolastatin 11 itself.
    Type
    text
    Dissertation-Reproduction (electronic)
    Degree Name
    Ph.D.
    Degree Level
    doctoral
    Degree Program
    Chemistry
    Graduate College
    Degree Grantor
    University of Arizona
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    Dissertations

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