Mark Wood | Biosciences | University of Exeter

Dr Mark Wood

Associate Professor in Organic Chemistry

M.E.Wood@exeter.ac.uk

3450

Geoffrey Pope 225

Geoffrey Pope Building, University of Exeter , Stocker Road, Exeter, EX4 4QD, UK

Overview

I am an organic chemist with research interests that cover a wide range of aspects of synthesis. Recent studies have focused on asymmetric synthesis of structurally complex amino acids, using what has proved to be a very versatile radical-based methodology and also the use of structurally unusual heterocycles for masking the reactivity of synthetically valuable functional groups. In this area, we have developed a methodology for the incorporation of protected isocyanates into organic molecules and this chemistry is being applied to the synthesis of a diverse set of biologically important, nitrogen-containing heterocycles. My teaching activities cover all aspects of organic chemistry from basic structure and bonding in organic molecules, to complex organic synthesis. I am a member of the Biological Chemistry research group.

Qualifications

1990 DPhil Organic Chemistry, University of Oxford
1989 MA Chemistry, Balliol College, University of Oxford
1986 BA (Hons) Chemistry, Balliol College, University of Oxford

Career

2022-present Associate Professor in Organic Chemistry, Biosciences, University of Exeter

2007-2022 Senior Lecturer in Organic Chemistry, Biosciences, University of Exeter

2005-2007 Lecturer in Organic Chemistry, Biosciences, University of Exeter
1996-2005 Lecturer in Organic Chemistry, School of Chemistry, University of Exeter
1990-1996 GlaxoWellcome (originally Glaxo) Fellow and Tutor in Organic Chemistry, St Catherine's College, University of Oxford)

Research group links

Cellular and Chemical Biology

Research

Research interests

The use of radical-based methodology in the synthesis of highly substituted amines and amino acids. The aim of these studies has been to develop a much-needed general synthetic route to amino acids (and other amine derivatives) possessing a quaternary chiral centre alpha-to the nitrogen atom and in particular, alpha,alpha-disubstituted alpha-amino acids. The central theme of this methodology is the formation of alpha-aminoalkyl radicals from existing amino acid and alpha-amino alcohol derivatives by 1,5-hydrogen atom transfer and the subsequent trapping of these radicals with appropriate radicalphiles, thus generating quaternary centres with high efficiency and excellent stereocontrol. This ongoing area of research has led to further investigations into the 1,5-hydrogen atom transfer process and in particular, studies into the effectiveness of deuterium as a protecting group for C-H bonds in radical and carbene chemistry.

Synthetic applications of structurally 'unusual' heterocycles. The second major area of my group's research has involved studies into the use of structurally "unusual" heterocycles as protected, reactive functional groups in organic synthesis. In particular, we have developed methods for the stereoselective incorporation of the 1,2,4-dithiazolidine-3,5-dione (Dts imide) moiety into molecules as a masked isocyanate equivalent. These studies have also revealed intriguing and unexpected physical properties associated with the parent imide heterocycle (particularly in terms of its acidity) and as a result, studies involving related heterocycles are proposed.

Investigation of photoinitiated Bergman cyclisation reactions using high-resolution laser spectroscopy. The importance of the Bergmann cyclisation reaction in the mode of action of anti-tumour enediyne antibiotics such as calicheamicin-alpha and the neocarzinostatins provided the starting point for this collaborative project for which Dr David Smith is the principal investigator. Whilst much has been written about this reaction, relatively little characterisation has been carried out on the reaction intermediates. My involvement in this project is from the synthetic angle, and I am currently directing and supervising the preparation of the required enediyne cyclisation precursors.

Research grants

2004 AstraZeneca
CASE Studentship � "New, Heterocyclic Routes to Protected Isocyanates and Ketenes"
2004 ESRC
"Investigation of Photoinitiated Bergman Cyclisation Reactions Using High-Resolution Laser Spectroscopy"
2004 Pfizer
"Synthesis of Amino Acids"
2003 ESRC
"Deuterium � A Remarkably Simple, Recyclable Protection Protocol in Radical and Carbene Chemistry"
2001 Celltech (subsequently UCB Group)
"A Versatile Methodology for the Preparation of Highly Substituted Amine Derivatives Including the Use of Deuterium as a Recyclable Protecting Group"

External Engagement and Impact

Committee/panel activities

Member of the EPSRC Peer Review College from 1st January 2006

Editorial responsibilities

Member of the Panel of Referees for Tetrahedron Letters (Elsevier) from 1st January 2004

Invited lectures

Some Radical and Some Not So Radical Heterocyclic Chemistry - Liverpool University, 5th December 2001

Some Radical and Some Not So Radical Heterocyclic Chemistry - Celltech, Cambridge, 28th March 2002

New Uses for Old Heterocycles - York University, 4th December 2002

New Uses for Old Heterocycles - Manchester University, 29th January 2003

A New Use for an Old Heterocycle - Gregynog Synthesis Society Meeting, 28th September 2003

New Uses for Some Old Heterocycles - Royal Society of Chemistry Organic Division Heterocyclic Group Meeting, Imperial College, London, 9th January 2004

Some Radical and Some Not So Radical Heterocyclic Chemistry - University of Loughborough, 9th February 2005

Some Radical and Some Not So Radical Heterocyclic Chemistry - University of St Andrews, 31st August 2005

Some Radical and Some Not So Radical Heterocyclic Chemistry - Cardiff University, 8st December 2005

Protection of C-H Bonds: The Story so Far" - South-West Regional Meeting of the Organic Division of the Royal Society of Chemistry, Cardiff University, 19th December 2005

New Uses for Old Heterocycles - Maybridge, Tintagel, 2nd May 2007

Media Coverage

Media coverage for collaborative research project with Exeter Medical School and King's College, London in the Daily Telegraph (30th April 2013 - apparently not on-line) and Daily Mail:

http://www.dailymail.co.uk/health/article-2335450/Stink-bomb-gas-hydrogen-sulphide-soothe-creaky-old-joints.html

Also covered in the Exeter Express and Echo and Western Morning News.

Teaching

Year 1
Nature of Organic Compounds (Stereochemistry)

Year 2
Structure, Reactivity and Synthesis of Organic Compounds (Carbonyl chemistry), Organic Polymers (Structure, synthesis and reactivity)

Year 3
Advanced Reactivity and Stereocontrol (Free-radical chemistry), Biological Chemistry (Amino acid and carbohydrate chemistry)

Year 4
Modern Strategies in Organic Chemistry (Organotransition metal chemistry)