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ISBN 9783843919142

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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

Zusammenfassung / Abstract

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.