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Towards the total synthesis of amphidinolide T family

Labre, Flavien (2012) Towards the total synthesis of amphidinolide T family. PhD thesis, University of Glasgow.

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Abstract

Amphidinolides T are challenging natural targets for the total synthesis community because of their unique structural architecture. This thesis describes the investigations of the establishment of a novel and convenient route to synthesise four members of the natural product family, amphidinolides T1 and T3-5, from a common late-stage intermediate. The key transformations towards the synthetic pathway are ring formation reactions. The trans-tetrahydrofuran ring is forged efficiently via diastereoselective [2,3]-sigmatropic rearrangement of an oxonium ylide from diazo-generated metal carbenoids. Coupling of a side chain is achieved using a sequence of esterification and RCM reactions. Alternatively, a one-pot RCM followed by hydrogenation is described to shorten the synthetic route.

Item Type: Thesis (PhD)
Qualification Level: Doctoral
Keywords: total synthesis, sigmatropic rearrangement, metathesis, amphidinolide, natural product
Subjects: Q Science > QD Chemistry
Q Science > Q Science (General)
Colleges/Schools: College of Science and Engineering > School of Chemistry
Supervisor's Name: Clark, Prof. Stephen James
Date of Award: 2012
Depositing User: Mr flavien labre
Unique ID: glathesis:2012-3642
Copyright: Copyright of this thesis is held by the author.
Date Deposited: 19 Oct 2012
Last Modified: 10 Dec 2012 14:09
URI: http://theses.gla.ac.uk/id/eprint/3642

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