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Title: Synthesis of the originally proposed structure of palmerolide C
Author: Wlochal, Joanna
ISNI:       0000 0004 2738 1034
Awarding Body: University of St Andrews
Current Institution: University of St Andrews
Date of Award: 2012
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The palmerolides are an emerging class of polyketide natural products isolated from marine organisms inhabiting the Antarctic Sea. Although there has been a substantial effort to prepare the most active family member palmerolide A, no synthetic work has been performed in the area of the other members of the family; palmerolides B and C of different ring structure. These compounds are particularly interesting due to their complex structures with undefined stereochemistry and both display high selectivity towards human melanoma cancer cell lines. A highly convergent strategy to access palmerolide C has been developed, relying on the assembly of three fragments using key bond couplings at C6-C7 (boron-mediated aldol reaction/dehydration) and C14-C15 (Julia-Kocienski olefination), followed by a suitable macrolactonisation step and Buchwald enamide formation. Prior to subunit synthesis, the relative configuration of the C8-C10 stereotriad was resolved via the synthesis of diastereomeric degradation fragments by the application of organocatalytic cross aldol reactions and a suitable 1,3-selective reduction.
Supervisor: Florence, Gordon J. Sponsor: Engineering and Physical Sciences Research Council
Qualification Name: Thesis (Ph.D.) Qualification Level: Doctoral
EThOS ID:  DOI: Not available