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Title: Studies on the total synthesis of radicicol and its analogues
Author: Lachs, Jennifer
Awarding Body: Imperial College London
Current Institution: Imperial College London
Date of Award: 2013
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Recent research has shown radicicol (I) to be a potent and selective inhibitor of Hsp90, stimulating a renewed interest in this natural product.i,ii Using a new latestage aromatisation strategy developed in the group, a concise and convergent formal synthesis of radicicol (I) was achieved. Formation of the 14-membered macrocycle relied on a relay-ring-closing metathesis (RRCM) of precursor II using the 2nd generation Hoveyda-Grubbs catalyst. The key late-stage aromatisation sequence consisting of the thermal retro-Diels-Alder reaction of III followed by ketene trapping with IV was used to construct the aromatic resorcylate framework of II. The aromatic chlorination is literature-known, therefore the formal synthesis was completed.iii Studies were also carried out towards the synthesis of potentially active analogues using the same strategy which was applied to the formal synthesis of radicicol (I).
Supervisor: Barrett, Anthony Sponsor: Not available
Qualification Name: Thesis (Ph.D.) Qualification Level: Doctoral
EThOS ID:  DOI: Not available