Graduate Thesis Or Dissertation
 

Synthesis of epothilones and epothilone analogues

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https://ir.library.oregonstate.edu/concern/graduate_thesis_or_dissertations/d791sk594

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  • A convergent synthesis of epothilone B that generates all seven of its asymmetric centers in a completely stereoselective fashion has been completed. Key reactions include an anti-Felkin aldol condensation to set the C6 and C7 stereochemistry, a directed α-hydroxylation to install the C15 (S)-hydroxyl substituent, and a Wittig condensation to join two main subunits via C-C bond formation at C9-C10. In addition, through modifications to the C9-C10 region of the macrolide, several novel and cytotoxic epothilone analogues were synthesized. Bioassay data comparing the antiproliferative activity and tubulin polymerization of the analogues with epothilone B, epothilone D, and paclitaxel showed that the synthetic analogues were less potent than their natural counterparts.
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