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978-3-8439-1914-2, Reihe Organische Chemie
Nils Martin Hülsken Untersuchungen zur enantioselektiven Totalsynthese von Mumbaistatin
211 Seiten, Dissertation Universität Köln (2014), Softcover, A5
The structural unique polyketide Mumbaistatin is an efficient inhibitor of the enzyme glucose-6-phosphate translocase 1 (G6P T1). Involvement of this enzyme in processes related to Diabetes mellitus and Glioblastoma growth emphasizes the pharmacological importance of this natural compound.
This work describes the convergent synthesis of a spiro deoxy derivative of this natural product utilizing a Diels-Alder-reaction to construct the anthraquinone moiety and an anionic homo-Fries-rearrangement to access the spiroketal core motif. Moreover, the first enantioselective approach to the fully functionalized side chain of the molecule via CBS reduction and an allylation with a chrial Boron reagent is reported. Benzylic oxidation modell studies established on a previously synthesized spiroketal test-system could not have been applied to deoxyderivatives of the natural product. Other substrate-specific benzylic functionalizations have been tested, including intramolecular photoreduction and H-abstraction.