Use this URL to cite or link to this record in EThOS: http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.616716
Title: Total synthesis of cruentaren A
Author: Fouche, Marianne
Awarding Body: Imperial College London
Current Institution: Imperial College London
Date of Award: 2012
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Abstract:
Cruentaren A, a highly cytotoxic metabolite, which also inhibits F-ATPase, was synthesized using our recently developed methodology on resorcylic acid lactones natural products. [Molecular structure diagrams appear here. To view, please open pdf attachment] Alcohol A was prepared on a multigram scale in 13 steps starting from (S)-Roche ester and using highly stereoselective reactions such as Evans aldol reaction and asymmetric propargylation. [Molecular structure diagrams appear here. To view, please open pdf attachment] Key fragment B was synthesized in 11 steps from 1,3-propanediol. The 1,2-anti-configuration was installed with a Brown crotylation. Diketo-dioxinone D was generated from C-acylation between Weinreb amide B and keto-dioxinone C. Ketene generation by thermolysis followed by trapping with alcohol A and aromatization afforded resorcylate derivative E. [Molecular structure diagrams appear here. To view, please open pdf attachment] Finally after a sequence consisting of the following key steps: ring closing alkyne metathesis, coupling between amine G and acid H and Lindlar hydrogenation, cruentaren A was obtained.
Supervisor: Barrett, Anthony Sponsor: Not available
Qualification Name: Thesis (Ph.D.) Qualification Level: Doctoral
EThOS ID: uk.bl.ethos.616716  DOI: Not available
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