Studies towards the total synthesis of dictyoxetane

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http://eprints.org/relation/isVersionOf http://etheses.bham.ac.uk/id/document/3861 http://eprints.org/relation/isVolatileVersionOf http://etheses.bham.ac.uk/id/document/3861 http://eprints.org/relation/isIndexCodesVersionOf http://etheses.bham.ac.uk/id/document/3861 archive 4031 disk0/00/00/17/07 2011-07-04 08:48:15 2019-01-23 09:54:42 2011-07-19 16:40:34 thesis show duplicate_title_8184 duplicate_title Duplicate title to <span class="person"><span class="person_name">Sembayeva, Aliya</span></span> (2017). <a href="http://etheses.bham.ac.uk/cgi/users/home?screen=EPrint::View&eprintid=8184"><xhtml:em xmlns:xhtml="http://www.w3.org/1999/xhtml">Studies towards the total synthesis of dictyoxetane.</xhtml:em></a> University of Birmingham. M.Sc. 2019-01-15 03:30:30 discovered 1 Defaut benedicte Grainger Richard S. University of Birmingham Studies towards the total synthesis of dictyoxetane unpub QD 10col_ephy Dictyoxetane, a structurally novel diterpene, is related to the dollabellane class of natural products. Dictyoxetane contains a dioxatricyclic subunit that has never been encountered in any other natural product. This thesis describes studies towards a first total synthesis of dictyoxetane, based on a proposed intramolecular Paternò-Büchi [2+2] photocyclisation reaction between a ketone and a cyclic enol ether to generate the oxetane heterocycle of the natural product. Chapter 1 introduces the dolabellanes. The isolation, structure and proposed biosynthesis of dictyoxetane are discussed, along with existing synthetic studies towards the core dioxatricyclic ring system. Key aspects of the Paternò-Büchi reaction of alkenes with carbonyl compounds are presented. In Chapter 2 a model system, designed to test the key Paternò-Büchi [2+2] photocyclisation reaction, is proposed. A number of strategies are investigated for the overall conversion of the double bond of isopulegol into a six-membered ring enol ether. Chapter 3 describes studies towards the synthesis of the [4.3.0]-trans-hydrindane ring system contained within dictyoxetane, a structural feature that has yet to be addressed in the literature. Chapter 4 contains the experimental procedures and analytical data of all compounds prepared during the course of this study. 2011-07 2010-10 graduation eng This unpublished thesis/dissertation is copyright of the author and/or third parties. The intellectual property rights of the author or third parties in respect of this work are as defined by The Copyright Designs and Patents Act 1988 or as modified by any successor legislation. Any use made of information contained in this thesis/dissertation must be in accordance with that legislation and must be properly acknowledged. Further distribution or reproduction in any format is prohibited without the permission of the copyright holder. public 200 University of Birmingham School of Chemistry d_ph na 2011-07 graduation