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Title: Studies toward the configurational assignment and total synthesis of reidispongiolide A
Author: Ashton, K. S.
Awarding Body: University of Cambridge
Current Institution: University of Cambridge
Date of Award: 2005
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Reidispongiolide A (10) is a cytotoxic, marine macrolide that exerts inhibition of cell growth through actin-binding. Of particular interest is its efficacy against multi-drug resistant cancer cell lines. At the outset of the project the stereochemical configuration of reidispongiolide A was uncertain and chemical degradation had been performed to enable further elucidation (Scheme A-1). Chapter 2 details the synthesis of possible diastereomers of the C23-C35 and C5-C16 degradation fragments 16 and 18. Identification of the correct diastereomer in each case allowed for a reduction in the number of possible diastereomers of reidispongiolide A from over a hundred to two. Chapter 3 uses the chemistry developed in the synthesis of the degradation fragments and applies this to the synthesis of the retrosynthetic fragments (Scheme A-2). Successful synthesis of the C14-C29 ketone 126 (16 steps, 34%) and a C6-C13 model aldehyde ent-168 allowed investigation of the pivotal C13-C14 aldol coupling (Scheme A-3). A Mukaiyama aldol reaction proved to be the best method and proceeded under Felkin control to give a 3:1 dr.
Supervisor: Not available Sponsor: Not available
Qualification Name: Thesis (Ph.D.) Qualification Level: Doctoral
EThOS ID:  DOI: Not available