Towards the total synthesis of a dolabellane diterpenoid, and studies in synthetic organic electrochemistry

<p>Chapter one begins with an introduction on the dolabellane diterpenoid natural product family, followed by a summary of the most recent total and formal syntheses of dolabellane diterpenoids. Previous work carried out in the Burton group towards the target natural product (1.5), a member of...

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Main Author: Mason, J
Other Authors: Robertson, J
Format: Thesis
Published: 2018
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author Mason, J
author2 Robertson, J
author_facet Robertson, J
Mason, J
author_sort Mason, J
collection OXFORD
description <p>Chapter one begins with an introduction on the dolabellane diterpenoid natural product family, followed by a summary of the most recent total and formal syntheses of dolabellane diterpenoids. Previous work carried out in the Burton group towards the target natural product (1.5), a member of the dolabellane family, will also be discussed. We then discuss our own work towards the natural product target 1.5. Significant progress towards the racemic natural product target has been achieved, and we have isolated the product 1.252 that derives from the key ring-closing metathesis reaction of 1.240. We have also achieved multi-gram syntheses of both enantiomers of an advanced intermediate in the natural product synthesis, and this work is detailed at the end of Chapter one. The synthesis of both enantiomers of the target natural product will be crucial in confirming the absolute configuration of the target natural product, 1.5. Chapter two is focused on the field of synthetic organic electrochemistry, and the work that we have done using this synthetic tool. Although we were ultimately unsuccessful in our stated aim of replacing the manganese(III) based oxidant in the radical cyclisation of substrates containing a dicarbonyl functional group, several observations were made which we expect will guide future research in this area.</p>
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spelling oxford-uuid:67fd6929-3f92-4ad6-a4a3-b3c1ef9c4da72022-03-26T18:41:57ZTowards the total synthesis of a dolabellane diterpenoid, and studies in synthetic organic electrochemistryThesishttp://purl.org/coar/resource_type/c_db06uuid:67fd6929-3f92-4ad6-a4a3-b3c1ef9c4da7ORA Deposit2018Mason, JRobertson, JBurton, JFox, D<p>Chapter one begins with an introduction on the dolabellane diterpenoid natural product family, followed by a summary of the most recent total and formal syntheses of dolabellane diterpenoids. Previous work carried out in the Burton group towards the target natural product (1.5), a member of the dolabellane family, will also be discussed. We then discuss our own work towards the natural product target 1.5. Significant progress towards the racemic natural product target has been achieved, and we have isolated the product 1.252 that derives from the key ring-closing metathesis reaction of 1.240. We have also achieved multi-gram syntheses of both enantiomers of an advanced intermediate in the natural product synthesis, and this work is detailed at the end of Chapter one. The synthesis of both enantiomers of the target natural product will be crucial in confirming the absolute configuration of the target natural product, 1.5. Chapter two is focused on the field of synthetic organic electrochemistry, and the work that we have done using this synthetic tool. Although we were ultimately unsuccessful in our stated aim of replacing the manganese(III) based oxidant in the radical cyclisation of substrates containing a dicarbonyl functional group, several observations were made which we expect will guide future research in this area.</p>
spellingShingle Mason, J
Towards the total synthesis of a dolabellane diterpenoid, and studies in synthetic organic electrochemistry
title Towards the total synthesis of a dolabellane diterpenoid, and studies in synthetic organic electrochemistry
title_full Towards the total synthesis of a dolabellane diterpenoid, and studies in synthetic organic electrochemistry
title_fullStr Towards the total synthesis of a dolabellane diterpenoid, and studies in synthetic organic electrochemistry
title_full_unstemmed Towards the total synthesis of a dolabellane diterpenoid, and studies in synthetic organic electrochemistry
title_short Towards the total synthesis of a dolabellane diterpenoid, and studies in synthetic organic electrochemistry
title_sort towards the total synthesis of a dolabellane diterpenoid and studies in synthetic organic electrochemistry
work_keys_str_mv AT masonj towardsthetotalsynthesisofadolabellanediterpenoidandstudiesinsyntheticorganicelectrochemistry