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Studies towards the total synthesis of dictyoxetane

Defaut, benedicte (2011)
Ph.D. thesis, University of Birmingham.

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Abstract

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.

Type of Work:Ph.D. thesis.
Supervisor(s):Grainger, Richard S.
School/Faculty:Colleges (2008 onwards) > College of Engineering & Physical Sciences
Department:School of Chemistry
Subjects:QD Chemistry
Institution:University of Birmingham
ID Code:1707
This unpublished thesis/dissertation is copyright of the author and/or third parties.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.
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