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Title: Towards the total synthesis of litophynol B : development of a butane-2,3-diacetal desymmetrized glycolate equivalent
Author: Guy, R. T.
Awarding Body: University of Cambridge
Current Institution: University of Cambridge
Date of Award: 2005
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This thesis describes the application of a butane-2,3-diacetal desymmetrized glycolate equivalent to the total synthesis of litophynol B and the development of this glycolate equivalent that occurred as a result. It is divided into seven chapters. Chapter 1 introduces litophynol B, reviews literature studies of related natural products, and summarises the glycolate chemistry that was known when this project was first undertaken. Chapter 2 describes the Ley Group approach towards litophynol B. Chapter 3 describes the synthesis of cryptone, an enone used in the total synthesis. Chapter 4 describes the progress made towards the synthesis of an aldehyde fragment. Chapter 5 describes the kinetic resolution of racemic cryptone by Michael addition of the glycolate, the attempts that were made to couple these adducts with aldehydes and deprotect the BDA group, as well as some novel glycolate methodology that was discovered.
Supervisor: Not available Sponsor: Not available
Qualification Name: Thesis (Ph.D.) Qualification Level: Doctoral
EThOS ID:  DOI: Not available