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ISBN 9783843920605

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978-3-8439-2060-5, Reihe Organische Chemie

Sebastian Wünsch
Total Synthesis of Dictyostatin

436 Seiten, Dissertation Albert-Ludwigs-Universität Freiburg im Breisgau (2014), Softcover, A5

Zusammenfassung / Abstract

The Ph.D. thesis presents a robust total synthesis of dictyostatin. This polyketide natural product has attracted much attention because of its impressive antiproliferative activity against several human cancer cell lines. Its synthesis was accomplished in a highly convergent manner from three fragments of equal complexity, which were prepared on multigram scale. The southern and northwestern subunits were constructed via o-DPPB-directed hydroformylation and allylic substitution, respectively. These methods generated the C6 and C14 stereocenters of dictyostatin with good diastereoselectivities and simultaneously allowed further elaboration of the fragments by Wittig olefination and Sharpless asymmetric epoxidation, respectively. The compelling performance of the hydroformylation and allylic substitution with regard to practicability, selectivity, and scale underline their value for the construction of propionate motifs.