Synthetic Investigations towards the Total Synthesis of Neuroprotective Natural Products

This thesis describes synthetic work undertaken towards the synthesis of the neuroprotective natural products mescengricin (12), palmyrolide A (13) and sanctolide A (14). Investigations towards the synthesis of mescengricin (12) were initially directed towards cyclisation of diarylamines 175. Attempts were made to elaborate diarylamines 175 with a view to produce the tricyclic α-carboline core of 12 via cyclisation to form the central pyrrole ring. Difficulties effecting the cyclisation of 175 led us to further investigate the electronic properties of the diarylamines 175. Completion of an important model study led to the synthesis of simplified α-carboline (15) by employing the photocyclisation of diarylamine 167. The total synthesis of the macrocyclic N-methyl enamide palmyrolide A (13f) is next reported. This was achieved using of a unique ring closing metathesis (RCM)/olefin isomerisation methodology that installed the key tertiary enamide functionality. With the successful completion of the synthesis of palmyrolide A (13f) an analogous RCM/olefin isomerisation strategy was used to effect the synthesis of the related macrolide sanctolide A (14a).

Name thesis:degree_name

PhD

Level thesis:degree_level

Doctoral

Grantor dc:publisher

ResearchSpace@Auckland

Year dc:date.issued

2014

Author dc:creator

• Wadsworth, Andrew

Advisors dc:contributor.advisor

• Brimble, M
• Sperry, J
• Furkert, D

Statement dc:rights

• Items in ResearchSpace are protected by copyright, with all rights reserved, unless otherwise indicated. Previously published items are made available in accordance with the copyright policy of the publisher.

Licence dc:rights.uri

• https://researchspace.auckland.ac.nz/docs/uoa-docs/rights.htm

Handle dc:identifier.uri

https://hdl.handle.net/2292/22392

OAI identifier oai:identifier

oai:researchspace.auckland.ac.nz:2292/22392