| Summary: | <p>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.</p>
<p><b>Chapter 1</b> introduces a review of literature reports relating to the biological activity and synthetic strategies to access dihydroconduramines and conduramines.</p>
<p><b>Chapter 2</b> 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.</p>
<p><b>Chapter 3</b> 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. </p>
<p><b>Chapter 4</b> details the asymmetric synthesis of four new enantiopure dihydroconduramines from an appropriate enantiopure anti-2 aminocyclohex-3-en-1-ols.</p>
<p><b>Chapter 5</b> details the asymmetric synthesis of six enantiopure dihydroconduramines from an appropriate enantiopure syn-2 aminocyclohex-3-en-1-ols.</p>
<p><b>Chapter 6</b> 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.</p>
<p><b>Chapter 7</b> 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.</p>
<p><b>Chapter 8</b> contains full experimental procedures and characterisation for all compounds synthesised in chapter 2-7.</p>
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