Use this URL to cite or link to this record in EThOS: https://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.816664
Title: Ammonium-directed epoxidation in the asymmetric syntheses of dihydroconduramines and conduramines
Author: Da Silva Pinto, Solange
ISNI:       0000 0004 9355 6306
Awarding Body: University of Oxford
Current Institution: University of Oxford
Date of Award: 2019
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Abstract:
This thesis centres on the asymmetric syntheses of a family of synthetic products: dihydroconduramines and conduramines. The work aims to use the ammonium-directed epoxidation methodology as a key step in all cases. Chapter 1 introduces a review of literature reports relating to the biological activity and synthetic strategies to access dihydroconduramines and conduramines. Chapter 2 investigates the olefinic oxidation protocol of racemic N-protected anti- and syn-2-aminocyclohex-3-en-1-ols. Concise syntheses of racemic dihydroconduramines (±)-A-2 and (±)-C-2 are also presented. Chapter 3 describes the syntheses of enantiopure N-protected anti- and syn-2-aminocyclohex-3-en-1-ols in order to access enantiopure dihydroconduramines. Investigation of the surrogacy of these substrates to the racemate is also undertaken. Chapter 4 details the asymmetric synthesis of four new enantiopure dihydroconduramines from an appropriate enantiopure anti-2 aminocyclohex-3-en-1-ols. Chapter 5 details the asymmetric synthesis of six enantiopure dihydroconduramines from an appropriate enantiopure syn-2 aminocyclohex-3-en-1-ols. Chapter 6 investigates the olefinic oxidation protocol of primary, secondary and tertiary racemic allylic amino alcohols, derived from ring-opening of benzene oxide with primary, secondary and tertiary amines. Chapter 7 describes concise asymmetric syntheses of six conduramines, including four new, from enantiopure allylic amino alcohols, derived from ring-opening of benzene oxide with (R)-α-methylbenzylamine. Chapter 8 contains full experimental procedures and characterisation for all compounds synthesised in chapter 2-7.
Supervisor: Davies, Steve Sponsor: Not available
Qualification Name: Thesis (Ph.D.) Qualification Level: Doctoral
EThOS ID: uk.bl.ethos.816664  DOI: Not available
Keywords: Organic Chemistry
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