Associate Professor Gavin Edwards

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BIOGRAPHICAL DETAILS
PhD studies at Monash University with G B Deacon and D StC Black. Postdoctoral research at Imperial College with W B Motherwell, 1987-1989. SSP at Cambridge University in 1997 with Professor Steven Ley. Appointed Lecturer UNSW, 1990; Senior Lecturer UNSW 1999-.

2005 - Present. Director of Teaching, School of Chemistry
2011 - Associate Dean (Undergraduate Programs) Faculty of Science

RESEARCH INTERESTS
Our research covers a range of areas, from medicinal chemistry to organic synthetic methodology. Collaborative research with Dr Laurence Wakelin (Department of Physiology and Pharmacology, School of Medical Sciences) and Professor David Black (Chemistry) is being pursued looking at novel DNA binding agents for possible anticancer applications. Classes of compounds being investigated are as diverse as new ellipticine analogues, potential metallointercalation reagents and acridine-based DNA-threading drugs.

In the quest for new synthetic methods, we have developed the use of the free radical addition of arenesulfonyl halides to alkenes and alkynes giving iodosulfones and thence vinyl sulfones as a route to heterocyclic molecules. This key reaction has led to the development of a diastereoselective synthesis of simple heterocyclic assemblies, and further application to natural product synthesis is being investigated. We are also interested in heteroatoms as controlling elements in organic reactions, such as the use of phosphorus containing groups to activate dienophiles for Diels-Alder reactions.

Phone

+ 61 2 93854652

E-mail

g.edwards@unsw.edu.au

Location

School of Chemistry University of New South Wales Sydney NSW 2052 Dalton Building Room 106

Book Chapters | 2008

Edwards GL; Balasubramanian M; Murugan R, 2008, 'Six-membered Rings with One Phosphorous Atom', in Black DS; Katrizky AR; Ramsden CA; Scriven EFV; Taylor RJK (ed.), Comprehensive Heterocyclic Chemistry: Six Membered Rings with One Heteroatom with Fused Carbbocyclic Derivatives, Elsevier, Oxford, pp. 1003 - 1037
Journal articles | 2010

BLACK DS; CRAIG DC; EDWARDS GL; LAAMAN SM, 2010, 'ChemInform Abstract: Intramolecular Cycloaddition of 5-Alkenyl-1-pyrroline 1-Oxide-5-carboxylic Esters.', ChemInform, 29, pp. no - no, http://dx.doi.org/10.1002/chin.199844048

Journal articles | 2010

BLACK DS; EDWARDS GL; LAAMAN SM, 2010, 'ChemInform Abstract: Radical Cyclization from Alkenyl Oxaziridines.', ChemInform, 29, pp. no - no, http://dx.doi.org/10.1002/chin.199843130

Journal articles | 2010

Beeren S; Dabb SL; Edwards GL; Smith M; Willis AC; Messerle BA, 2010, 'Improving intramolecular hydroamination Rh(I) and Ir(I) catalysts through targeted ligand modification', New Journal of Chemistry, 34, pp. 1200 - 1208, http://dx.doi.org/10.1039/b9nj00759h

Journal articles | 2010

Black DS; Edwards GL; Evans RH; Keller PA; Laaman SM, 2010, 'ChemInform Abstract: Synthesis and Reactivity of 1-Pyrroline-5-carboxylate Ester 1-Oxides.', ChemInform, 31, pp. no - no, http://dx.doi.org/10.1002/chin.200026110

Journal articles | 2006

Black DS; Edwards GL; Laaman SM, 2006, 'Synthesis and Radical Reactions of Isomeric Alkenyl Oxaziridines.', ChemInform, 37, http://dx.doi.org/10.1002/chin.200641090

Journal articles | 2006

Black DS; Edwards GL; Laaman SM, 2006, 'Synthesis and radical reactions of isomeric alkenyl oxaziridines', SYNTHESIS-STUTTGART, pp. 1981 - 1990, http://dx.doi.org/10.1055/s-2006-9423

Journal articles | 2006

Edwards GL; Black DS; Laaman SM, 2006, 'Synthesis and radical reactions of isomeric alkenyl oxaziridines', Synthesis: Journal of Synthetic Organic Chemistry, pp. 1981 - 1990, http://dx.doi.org/10.1055/s-2006-942380

Journal articles | 2005

Edwards GL; Black DS; Deacon G; Wakelin L, 2005, 'Effect of charge and surface area on the cytotoxicity of cationic metallointercalation reagents', Canadian Journal of Chemistry - Revue Canadienne de Chimie, 83, pp. 969 - 979, http://dx.doi.org/10.1139/v05-110

Journal articles | 2005

Edwards GL; Black DS; Deacon G; Wakelin L, 2005, 'In vitro and in vivo studies of neutral cyclometallated complexes against murine leukaemias', Canadian Journal of Chemistry - Revue Canadienne de Chimie, 83, pp. 980 - 989, http://dx.doi.org/10.1139/v05-109

Journal articles | 2005

Edwards GL; Sinclair DJ, 2005, 'Sequential cyclosulfonylation and alkylation as a versatile strategy for dihydropyran synthesis', Synthesis: Journal of Synthetic Organic Chemistry, pp. 3613 - 3619, http://dx.doi.org/10.1055/s-2005-918498

Journal articles | 2001

Craig DC; Edwards GL; Sinclair DJ, 2001, 'A new synthesis of spiroketals via sulfonyl-substituted dihydropyrans', Tetrahedron, 57, pp. 563 - 570, http://dx.doi.org/10.1016/S0040-4020(00)01026-7

Journal articles | 2000

Black DS; Craig DC; Edwards GL; Laaman SM, 2000, 'Synthetic routes to tropanes and pyrrolizidines from nitrones and oxaziridines', ACGC Chemical Research Communications, 11, pp. 16 - 19

Journal articles | 2000

Black DS; Edwards GL; Evans R; Keller PA; Laaman SM, 2000, 'Synthesis and reactivity of 1-pyrroline-5-carboxylate ester 1-oxides', Tetrahedron, 56, pp. 1889 - 1897, http://dx.doi.org/10.1016/S0040-4020(00)00094-6

Journal articles | 2000

Buffet MF; Dixon D; Edwards GL; Ley SV; Tate E, 2000, 'Oxygen to carbon rearrangements of anomerically linked alkenols from tetrahydropyran derivatives: an investigation of the reaction mechanism via a double isotopic labelling crossover study', Journal of the chemical society, dalton transactions, 2000, pp. 1815 - 1827, http://dx.doi.org/10.1039/a909300a

Journal articles | 1999

Black DS; Craig DC; Edwards GL; Laaman SM, 1999, 'Versatile synthesis and reactivity of tropanes and related azabicycloalkanes', Bioorganic Chemistry, 27, pp. 91 - 99, http://dx.doi.org/10.1006/bioo.1998.1123

Journal articles | 1999

Edwards GL; Sinclair DJ, 1999, 'Alkylation of vinyl sulfones as a route to 2-alkylidene tetrahydrofurans', Tetrahedron Letters, 40, pp. 3933 - 3934, http://dx.doi.org/10.1016/S0040-4039(99)00573-0

Journal articles | 1998

Black DS; Craig DC; Edwards GL; Laaman SM, 1998, 'Intramolecular cycloaddition of 5-alkenyl-1-pyrroline 1-oxide-5-carboxylic esters', Tetrahedron Letters, 39, pp. 5849 - 5852, http://dx.doi.org/10.1016/S0040-4039(98)01159-9

Journal articles | 1998

Black DS; Edwards GL; Laaman SM, 1998, 'Radical cyclisation from alkenyl oxaziridines', Tetrahedron Letters, 39, pp. 5853 - 5856, http://dx.doi.org/10.1016/S0040-4039(98)01160-5

Journal articles | 1997

Buffet MF; Dixon D; Edwards GL; Ley SV; Tate E, 1997, 'A General C-Glycosidation Procedure via Anomeric Oxygen to Carbon Rearrangements of Tetrahydropyranyl Ether Derivatives', Synlett, 1997, pp. 1055 - 1056, http://dx.doi.org/10.1055/s-1997-1531

Journal articles | 1997

Craig DC; Edwards GL; Muldoon CA, 1997, 'A Stereoselective Approach to 2,6-Disubstituted Tetrahydropyrans by Conjugate Addition Reactions of Vinyl Sulfones', Synlett, 1997, pp. 1318 - 1320, http://dx.doi.org/10.1055/s-1997-1016

Journal articles | 1997

Craig DC; Edwards GL; Muldoon CA, 1997, 'Diastereoselective Synthesis of a,a¿-Disubstituted Oxygen Heterocycles', Tetrahedron, 53, pp. 6171 - 6182, http://dx.doi.org/10.1016/S0040-4020(97)00274-3

Journal articles | 1997

Craig DC; Edwards GL; Muldoon CA, 1997, 'Synthesis of 2-Substituted Nitrogen Heterocycles Using Para-Toluenesulfonyl Iodide in a Key Step', Synlett, pp. 1441 - 1443

Journal articles | 1997

Edwards GL; Sinclair DJ; Wasiowych CD, 1997, 'A New Route to Substituted Dihydropyrans', Synlett, 1997, pp. 1285 - 1286, http://dx.doi.org/10.1055/s-1997-1017

Journal articles | 1996

Edwards GL; Muldoon CA; Sinclair DJ, 1996, 'Cyclic enol ether synthesis via arenesulfonyl iodide additions to alkynols', Tetrahedron, 52, pp. 7779 - 7788, http://dx.doi.org/10.1016/S0040-4020(96)00346-8

Journal articles | 1995

Craig DC; Durie A; Edwards GL; Sinclair DJ, 1995, 'the cyclosulfonylation reaction: a comment on the radical reactions of 4-pentenyl tosylate', Tetrahedron Letters, 36, pp. 1307 - 1310, http://dx.doi.org/10.1016/0040-4039(94)02446-I

Journal articles | 1993

Black DSC; Edwards GL, 1993, 'Organomercury compounds. XXXI. Preparations and 199hg n.m.r. spectra of organomercury derivatives of 2-phenylpyridine, benzo[h]quinoline, 1-phenylpyrazole and 3, 4, 5-trimethyl-1-phenylpyrazole, and the x-ray crystal structure of bis[2-(pyridin-2'-yl)phenyl]mercury', Australian Journal of Chemistry, 46, pp. 1323 - 1336, http://dx.doi.org/10.1071/CH9931323

Journal articles | 1993

Childs BJ; Edwards GL, 1993, 'A non-enzymatic, asymmetric synthesis of dicyclopentadienone', Tetrahedron Letters, 34, pp. 5341 - 5342, http://dx.doi.org/10.1016/S0040-4039(00)73992-X

Journal articles | 1992

Edwards GL; Walker KA, 1992, 'para-toluenesulfonyl iodide as a convenient, mild reagent for the preparation of functionalised cyclic ethers', Tetrahedron Letters, 33, pp. 1779 - 1782, http://dx.doi.org/10.1016/S0040-4039(00)91731-3

Journal articles | 1991

Black DSC; Edwards GL, 1991, 'Synthesis of 7-substituted indoles as potential ligand precursors', Australian Journal of Chemistry, 44, pp. 1771 - 1781, http://dx.doi.org/10.1071/CH9911771
Conference Presentations | 2012

Gatus M; Messerle BA; Edwards GL, 2012, 'Homo- and Heterobimetallic Complexes for Tandem One-Pot Reactions', presented at 22nd Reactive Organometallics Symposium, University of New South Wales, Sydney, 19 November 2012

Conference Papers | 2010

Gatus M; Choy S; Messerle BA; Edwards GL, 2010, 'Multimetallic Rhodium(I) Complexes for the Dihydroalkoxylation Reaction', in Multimetallic Rhodium(I) Complexes for the Dihydroalkoxylation Reaction, 18th Reactive Organometallic Symposium, UNSW, Sydney, Australia, pp. 7 - 7, presented at 18th Reactive Organometallic Symposium, UNSW, Sydney, Australia, 19 November 2010

Conference Papers | 2010

Gatus M; Messerle BA; Edwards GL, 2010, 'The Synthesis of Iridium and Rhodium Multimetallic Catalysts and Their Use in Dihydroalkoxylation of Alkynediols', in The Synthesis of Iridium and Rhodium Multimetallic Catalysts and Their Use in Dihydroalkoxylation of Alkynediols, 17th Reactive Organometallic Symposium, ANU, Canberra, Australia, presented at 17th Reactive Organometallic Symposium, ANU, Canberra, Australia, 11 June 2010

Conference Papers | 2008

Khazaly AN; He Z; Stewart BW; Edwards GL; Wakelin L, 2008, 'Bisintercalating threading agents as cytotoxic inhibitors of transcription', in EJC Supplements, Pergamon-Elsevier Science Ltd, Kidlington, Oxford, England, pp. 83 - 84, presented at 20th Meeting of the European Association for Cancer Research, Lyon, FRANCE, 05 July 2008 - 08 July 2008, http://dx.doi.org/10.1016/S1359-6349(08)71498-8

Conference Papers | 2008

Nguyen OT; Hodgson R; Messerle BA; Edwards GL, 2008, 'Metal Complexes Containing N-N Ligands for Catalysis', in Abstract book, 14th Reactive Organometallic Symposium: ROMS14, Sydney, Australia, pp. 4 - 4, presented at 14th Reactive Organometallic Symposium: ROMS14, Sydney, Australia, 20 June 2008

Conference Papers | 2006

Edwards GL; Black DS; Deacon G; Wakelin L, 2006, 'Cycometallated platinum and palladium complexes as anticancer agents: Everything old is new again', in Australia and New Zealand Symposium on Organometallic Chemistry OZOM3, 3rd Australian and New Zealand Symposium on Oranometallic Chemistry, Monash university, Gippsland, Australia, pp. 47 - 47, presented at 3rd Australian and New Zealand Symposium on Oranometallic Chemistry, Monash university, Gippsland, Australia, 08 January 2006 - 11 January 2006