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Tandem [3,3] Sigmatropic Rearrangements for Bioactive Alkaloid Synthesis.

1982 …2019
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Research Output 1982 2019

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Article
2019

Chemoenzymatic Synthesis of (-)-Ribisins A and B from Dibenzo[b,d]furan

Boyd, D. R., Sharma, N. D., McGivern, C. J., Stevenson, P. J., Hoering, P. & Allen, C. C. R., 06 Dec 2019, In : Journal of Organic Chemistry. 84, p. 15165- 15172 8 p.

Research output: Contribution to journalArticle

Metabolites
Biological Products
Carbon
Aromatic compounds
Functional groups
2 Citations (Scopus)

cis‐Dihydroxylation of Tricyclic Arenes and Heteroarenes Catalyzed by Toluene Dioxygenase: A Molecular Docking Study and Experimental Validation

Boyd, D., Sharma, N. D., Brannigan, I., McGivern, C., Nockemann, P., Stevenson, P., McRoberts, C., Hoering, P. & Allen, C. C. R., 18 Mar 2019, In : Advanced Synthesis & Catalysis.

Research output: Contribution to journalArticle

Metabolites
Phenol
Derivatives
Crystallography
Epoxy Compounds
2018
1 Citation (Scopus)

Enantiopurity and absolute configuration determination of arene cis-dihydrodiol metabolites and derivatives using chiral boronic acids

Boyd, D. R., Sharma, N. D., Goodrich, P. A., Malone, J. F., McConville, G., Harrison, J. S., Stevenson, P. J. & Allen, C. C. R., Jan 2018, In : Chirality. 30, 1, p. 5-18

Research output: Contribution to journalArticle

Boronic Acids
Metabolites
Derivatives
Acids
Alkenes
10 Citations (Scopus)

The effect of chiral doping in achiral smectic liquid crystals on the de Vries characteristics: smectic layer thickness, electro-optics and birefringence

Swaminathan, V., Panov, V. P., Panarin, Y. P., Sreenilayam, S. P., Vij, J. K., Panov, A., Rodriguez-Lojo, D., Stevenson, P. J. & Gorecka, E., 16 Mar 2018, In : Liquid Crystals. 45, 4, p. 513-521 9 p.

Research output: Contribution to journalArticle

Smectic liquid crystals
Electrooptical effects
Birefringence
electro-optics
birefringence
2017
9 Citations (Scopus)
167 Downloads (Pure)

Chiral smectic-A and smectic-C phases with de Vries characteristics

Stevenson, P., 21 Jun 2017, In : Physical Review E. 95, 6, 9 p., 062704.

Research output: Contribution to journalArticle

Open Access
File
Tilt
Order Parameter
Angle
Infrared Spectroscopy
Cell
8 Citations (Scopus)

Design and investigation of de Vries liquid crystals based on 5-phenyl-pyrimidine and (R,R)-2,3-epoxyhexoxy backbone

Sreenilayam, S. P., Rodriguez-Lojo, D., Panov, V. P., Swaminathan, V., Vij, J. K., Panarin, Y. P., Gorecka, E., Panov, A. & Stevenson, P. J., 03 Oct 2017, In : Physical Review E. 96, 4, 13 p., 042701.

Research output: Contribution to journalArticle

pyrimidines
Shrinkage
Backbone
shrinkage
Liquid Crystal
4 Citations (Scopus)
107 Downloads (Pure)

Enzyme-Catalysed Synthesis of Cyclohex-2-en-1-one cis-Diols from Substituted Phenols, Anilines and Derived 4-Hydroxycyclohex-2-en-1-ones

Boyd, D. R., Sharma, N. D., McIntyre, P. B. A., Stevenson, P. J., McRoberts, W. C., Gohil, A., Hoering, P. & Allen, C., 23 Nov 2017, In : Advanced Synthesis and Catalysis. 359, 22, p. 4002-4014 13 p.

Research output: Contribution to journalArticle

Open Access
File
Aniline Compounds
Phenols
Metabolites
Phenol
Enzymes
4 Citations (Scopus)
133 Downloads (Pure)

Observation of the de Vries behavior in SmA∗ phase of a liquid crystal using polarised Raman scattering and infrared spectroscopy

Kocot, A., Vij, J. K., Perova, T. S., Merkel, K., Swaminathan, V., Sreenilayam, S. P., Yadav, N., Panov, V. P., Stevenson, P. J., Panov, A. & Rodriguez-Lojo, D., 01 Sep 2017, In : Journal of Chemical Physics. 147, 9, 094903.

Research output: Contribution to journalArticle

Open Access
File
Liquid Crystals
Distribution functions
Raman scattering
Cones
Infrared spectroscopy
12 Citations (Scopus)

Phase behavior and characterization of heptamethyltrisiloxane-based de Vries smectic liquid crystal by electro-optics, x rays, and dielectric spectroscopy

Sreenilayam, S. P., Agra-Kooijman, D. M., Panov, V. P., Swaminathan, V., Vij, J. K., Panarin, Y. P., Kocot, A., Panov, A., Rodriguez-Lojo, D., Stevenson, P. J., Fisch, M. R. & Kumar, S., 10 Mar 2017, In : Physical Review E. 95, 3, 11 p., 032701.

Research output: Contribution to journalArticle

Electro-optics
shrinkage
Liquid Crystal
electro-optics
Spectroscopy
2016
8 Citations (Scopus)
127 Downloads (Pure)

Anomalous temperature dependence of layer spacing of de Vries liquid crystals: Compensation model

Merkel, K., Kocot, A., Vij, J. K., Stevenson, P. J., Panov, A. & Rodriguez, D., 13 Jun 2016, In : Applied Physics Letters. 108, 24, 243301.

Research output: Contribution to journalArticle

Open Access
File
liquid crystals
spacing
temperature dependence
shrinkage
temperature
2015
6 Citations (Scopus)

Arene cis-Diol Dehydrogenase-Catalysed Regio- and Stereoselective Oxidation of Arene-, Cycloalkane- and Cycloalkene-cis-diols to Yield Catechols and Chiral α-Ketols

Boyd, D. R., Sharma, N. D., Berberian, M. V., Cleij, M., Hardacre, C., Ljubez, V., McConville, G., Stevenson, P. J., Kulakov, L. A. & Allen, C. C. R., 26 May 2015, In : Advanced Synthesis and Catalysis. 357, 8, p. 1881-1894 14 p.

Research output: Contribution to journalArticle

12 Citations (Scopus)

Toluene Dioxygenase Catalysed synthesis and reactions of cis-diol metabolites derived from 2 and 3-methoxy phenols

Boyd, D. R., Sharma, N. D., Malone, J. F., McIntyre, P. B. A., McRoberts, C., Floyd, S., Allen, C. C. R., Gohil, A., Coles, S. J., Horton, P. N. & Stevenson, P. J., 2015, In : Journal of Organic Chemistry. 80, 7, p. 3429-3429 11 p.

Research output: Contribution to journalArticle

Phenols
Metabolites
Aromatization
Methylation
Phenol
2014
2 Citations (Scopus)

Convergence of products from Povarov and von Miller reactions: approaches to helquinoline

Stevenson, P. J., He, P. & Daly, B., 07 Oct 2014, In : Tetrahedron. 70, 40, p. 7350-7357 8 p.

Research output: Contribution to journalArticle

2 Citations (Scopus)

Reactions of enantiopure cyclic diols with sulfuryl chloride

Boyd, D. R., Sharma, N. D., Kaik, M., McIntyre, P. B. A., Malone, J. F. & Stevenson, P. J., 26 Feb 2014, In : Organic and Biomolecular Chemistry. 12, 13, p. 2128-2136 9 p.

Research output: Contribution to journalArticle

2013
5 Citations (Scopus)

Chemoenzymatic synthesis of monocyclic arene oxides and arene hydrates from substituted benzene substrates

Boyd, D. R., Sharma, N. D., Ljubez, V., McGeehin, P. K. M., Stevenson, P. J., Blain, M. & Allen, C. C. R., 26 Mar 2013, In : Organic and Biomolecular Chemistry. 11, 18, p. 3020-3029

Research output: Contribution to journalArticle

22 Citations (Scopus)
312 Downloads (Pure)

Chiral thiouronium salts: synthesis, characterisation and application in NMR enantio-discrimination of chiral oxoanions

Foreiter, M. B., Gunaratne, H. Q. N., Nockemann, P., Seddon, K. R., Stevenson, P. J. & Wassell, D. F., Feb 2013, In : New journal of chemistry. 37, 2, p. 515-533

Research output: Contribution to journalArticle

Open Access
File
5 Citations (Scopus)

Reactions of nitrogen nucleophiles with enantiopure cyclohexenyl electrophiles: a stereo- and regio- selective study

Boyd, D. R., Sharma, N. D., Belhocine, T., Malone, J. F., McGregor, S. T., Atchison, J., McIntyre, P. A. B. & Stevenson, P. J., Dec 2013, In : Journal of Physical Organic Chemistry. 26, 12, p. 997-1008 12 p.

Research output: Contribution to journalArticle

2012
19 Citations (Scopus)
159 Downloads (Pure)

Chemoenzymatic formal synthesis of (-)- and (+)-epibatidine

Boyd, D. R., D. Sharma, N., Kaik, M., McIntyre, P. B. A., Stevenson, P. J. & Allen, C. C. R., 2012, In : Organic and Biomolecular Chemistry. 10, 14, p. 2774-2779 6 p.

Research output: Contribution to journalArticle

Open Access
File
epibatidine
pseudomonas
enantiomers
microorganisms
palladium
14 Citations (Scopus)

Chemoenzymatic synthesis of a mixed phosphine-phosphine oxide catalyst and its application to asymmetric allylation of aldehydes and hydrogenation of alkenes

Boyd, D. R., Bell, M., Dunne, K. S., Kelly, B., Stevenson, P. J., Malone, J. F. & Allen, C., 21 Feb 2012, In : Organic and Biomolecular Chemistry. 10, 7, p. 1388-1395 8 p.

Research output: Contribution to journalArticle

phosphine
Allylation
Hydrogenation
Alkenes
aldehydes
30 Citations (Scopus)

Overcoming Equilibrium Issues with Carbonyl Reductase Enzymes

Calvin, S. J., Mangan, D., Miskelly, I., Moody, T. S. & Stevenson, P. J., 20 Jan 2012, In : Organic Process Research & Development. 16, 1, p. 82-86 5 p.

Research output: Contribution to journalArticle

Alcohol Oxidoreductases
purification
Purification
enzymes
Screening
8 Citations (Scopus)

Structure, stereochemistry and synthesis of enantiopure cyclohexenone cis-diol bacterial metabolites derived from phenols

Boyd, D. R., Sharma, N. D., Malone, J. F., McIntyre, P. M. A., Stevenson, P. J., Allen, C. C. R., Kwit, M. & Gawronski, J., 2012, In : Organic and Biomolecular Chemistry. 10, 30, p. 6217-6229 13 p.

Research output: Contribution to journalArticle

Stereochemistry
Enantiomers
metabolites
Phenols
X ray crystallography
7 Citations (Scopus)

Toluene dioxygenase-catalyzed cis-dihydroxylation of benzo[b]thiophenes and benzo[b]furans: synthesis of benzo[b]thiophene 2,3-oxide

Boyd, D. R., Sharma, N. D., Brannigan, I. N., Evans, T. A., Haughey, S. A., McMurray, B. T., Malone, J. F., McIntyre, P. B. A., Stevenson, P. J. & Allen, C. C. R., Sep 2012, In : Organic & biomolecular chemistry. 10, 36, p. 7292-7304 13 p.

Research output: Contribution to journalArticle

furans
thiophenes
Oxides
toluene
oxides
2011
9 Citations (Scopus)

Cycloalkenyl Halide Substitution Reactions of Enantiopure Arene cis-Tetrahydrodiols with Boron, Nitrogen and Phosphorus Nucleophiles

Boyd, D. R., Sharma, N. D., Kaik, M., Bell, M., Berberian, M. V., McIntyre, P. B. A., Kelly, B., Hardacre, C., Stevenson, P. J. & Allen, C. C. R., Sep 2011, In : Advanced Synthesis & Catalysis. 353, 13, p. 2455-2465 11 p.

Research output: Contribution to journalArticle

Rhodium
Nucleophiles
Halogens
Boron
Graphite
23 Citations (Scopus)
Immunosorbents
malachite
Metabolites
disequilibrium
Fish
24 Citations (Scopus)
1-phenylazo-2-naphthol
Spices
Immunosorbents
Permeation
Assays
16 Citations (Scopus)

Dioxygenase-catalysed cis-dihydroxylation of meta-substituted phenols to yield cyclohexenone cis-diol and derived enantiopure cis-triol metabolites

Boyd, D., Sharma, N., Stevenson, P., Blain, M., McRoberts, C., Hamilton, J., Argudo, J. M., Mundi, H., Kulakov, L. & Allen, C., 01 Mar 2011, In : Organic and Biomolecular Chemistry. 9, 5, p. 1479-1490 12 p.

Research output: Contribution to journalArticle

triols
Dioxygenases
metabolites
Phenols
Metabolites
7 Citations (Scopus)

Second-order NMR spectra at high field of common organic functional groups

Stevenson, P., 07 Apr 2011, In : Organic and Biomolecular Chemistry. 9, 7, p. 2078-2084 7 p.

Research output: Contribution to journalArticle

Functional groups
Sulfones
Protons
Nuclear magnetic resonance
nuclear magnetic resonance
2010
39 Citations (Scopus)

Chemoenzymatic Synthesis of Carbasugars (+)-Pericosines A-C from Diverse Aromatic cis-Dihydrodiol Precursors

Boyd, D., Sharma, N., Acaru, C., Malone, J., O'Dowd, C., Allen, C. & Stevenson, P., 21 May 2010, In : Organic Letters. 12, 10, p. 2206-2209 4 p.

Research output: Contribution to journalArticle

Carbasugars
Pseudomonas putida
pseudomonas
microorganisms
Biological Products
11 Citations (Scopus)

Chemoenzymatic synthesis of the carbasugars carba-beta-L-galactopyranose, carba-beta-L-talopyranose and carba-alpha-L-talopyranose from methyl benzoate

Boyd, D., Sharma, N., Bowers, N. I., Coen, G. B., Malone, J., O'Dowd, C., Stevenson, P. & Allen, C., 21 Mar 2010, In : Organic and Biomolecular Chemistry. 8, 6, p. 1415-1423 9 p.

Research output: Contribution to journalArticle

Carbasugars
metabolites
X ray crystallography
X Ray Crystallography
Metabolites
13 Citations (Scopus)

Synthesis and Reactions of Enantiopure Substituted Benzene cis-Hexahydro-1,2-diols

Boyd, D., Sharma, N., Berberian, V., Dunne, K. S., Hardacre, C., Kaik, M., Kelly, B., Malone, J., McGregor, S. T. & Stevenson, P., 22 Mar 2010, In : Advanced Synthesis & Catalysis. 352, 5, p. 855-868 14 p.

Research output: Contribution to journalArticle

phosphine
Cyclohexanols
Benzene
Hydrogenation
X ray crystallography
2009
3 Citations (Scopus)

Palladium-mediated reductive coupling, a stereoselective approach to the 8-dehydropumiliotoxin skeleton

Feutran, S. A., McAlonan, H., Stevenson, P. & Walker, A. D., 01 Jul 2009, In : Tetrahedron Letters. 50, 26, p. 3669-3671 3 p.

Research output: Contribution to journalArticle

Cyclization
Palladium
Skeleton
Stereochemistry
Acetates
2008
2 Citations (Scopus)
159 Downloads (Pure)

Facile synthesis of two diastereomeric indolizidines corresponding to the postulated structure of alkaloid 5,9E-259B from a Bufonid toad (Melanophryniscus)

Nelson, A., Garraffo, H. M., Spande, T. F., Daly, J. W. & Stevenson, P. J., 21 Jan 2008, In : Beilstein Journal of Organic Chemistry . 4, 6, 7 p.

Research output: Contribution to journalArticle

Open Access
File
Indolizidines
Stereochemistry
Biological Products
Alkaloids
Hydrogen
2007
20 Citations (Scopus)

Multi component coupling reactions of N-acetyl-2-azetine

Stevenson, P., Nieuwenhuyzen, M. & Osborne, D., 2007, In : Arkivoc. 11, 11, p. 129-144 16 p.

Research output: Contribution to journalArticle

Azetines
Cycloaddition
Amines
Quinolines
Lewis Acids
2006

Synthesis of the heterocyclic core of the alkaloids Martine line and Martinellic acid

Stevenson, P., Hadden, M., Nieuwenhuyzen, M., Osborne, D. & Thompson, N., 2006, In : Tetrahedron. 42, p. 6417-6419 3 p.

Research output: Contribution to journalArticle

2005
7 Citations (Scopus)

A revised structure for alkaloid 235C isolated from skin extracts of mantellid (Mantella) frogs of Madagascar

Andriamaharavo, N. R., Andriantsiferana, M., Stevenson, P., O'Mahony, G., Yeh, H. J. C., Kaneko, T., Garraffo, H. M., Spande, T. F. & Daly, J. W., Dec 2005, In : Journal of Natural Products. 68, 12, p. 1743-1748 6 p.

Research output: Contribution to journalArticle

Madagascar
Alkaloids
skin (animal)
Anura
frogs
5 Citations (Scopus)

Stereoselective synthesis of (8R,8aS)-8-methylhexahydroindolizin-5-one

Armstrong, P., O'Mahony, G., Stevenson, P. & Walker, A. D., 21 Nov 2005, In : Tetrahedron Letters, ISSN. 46, 47, p. 8109-8111 3 p.

Research output: Contribution to journalArticle

Indolizidines
Hydrogenation
Alkenes
Stereoselectivity
Oxidation

Use of cis-cyclohexanediols in synthesis.

Graham, I. P., Stevenson, P. & Boyd, D., 2005, In : Abstracts Of Papers Of The American Chemical Society. 229, p. U345-U345 1 p.

Research output: Contribution to journalArticle

2004
23 Citations (Scopus)

Rapid stereoselective access to key pumiliotoxin precursors from a common intermediate

Stevenson, P., Armstrong, P., O'Mahoney, G. & Nieuwenhuyzen, M., 28 Apr 2004, In : Journal of Organic Chemistry. 69(11), 11, p. 3968-3971 4 p.

Research output: Contribution to journalArticle

12 Citations (Scopus)

Synthesis of the putative structures of homopumiliotoxins 235C and 233F

Armstrong, P., Feutren, S., McAlonan, H., O'Mahony, G. & Stevenson, P., 16 Feb 2004, In : Tetrahedron Letters. 45, 8, p. 1627-1630 4 p.

Research output: Contribution to journalArticle

Quinolizidines
Biological Products
2003

Unprecedented regio and stereocontrol in Povarov reaction of benzylidene-(3-nitrophenyl) amine

Stevenson, P. & Graham, I., 2003, In : Arkivoc. 7, p. 139-144 6 p.

Research output: Contribution to journalArticle

Imines
Amines
Alkenes
Stereoselectivity
Regioselectivity
2002
62 Citations (Scopus)

4-Phenyloxazolidin-2-ones and isoindolin-1-ones; chiral auxiliaries for Diels-Alder reactions of N-substituted 1,3-dienes.

Stevenson, P., McAlonan, H., Murphy, J. P., Nieuwenhuyzen, M., Reynolds, K., Sarma, P. K. S. & Thompson, N., Jan 2002, In : Journal of the Chemical Society - Perkin Transactions 1. 1, 1, p. 69-79 11 p.

Research output: Contribution to journalArticle

67 Citations (Scopus)

A concise Formal Synthesis of Luotonin A.

Stevenson, P. & Osborne, D., 29 Jul 2002, In : Tetrahedron Letters. 43(31), 31, p. 5469-5470 2 p.

Research output: Contribution to journalArticle

9 Citations (Scopus)

Detection of cis-trans isomers of a synthetic peptide fragment of erythropoietin

Husain, R. D., McCandless, J., Stevenson, P., Large, T., Guthrie, D. J. S. & Walker, B., Jan 2002, In : JOURNAL OF CHROMATOGRAPHIC SCIENCE. 40, 1, p. 1-6 6 p.

Research output: Contribution to journalArticle

30 Citations (Scopus)

Three component coupling reactions of N-acetyl-2-azetine-rapid stereoselective entry to 2,3,4-trisubstituted tetrahydroquinolines

Stevenson, P., Nieuwenhuyzen, M. & Osborne, D., 07 Mar 2002, In : Chemical Communications. 5, 5, p. 444-445 2 p.

Research output: Contribution to journalArticle

Azetines
Amines
Lewis Acids
Imines
Cycloaddition
2001
70 Citations (Scopus)

Synthesis and reactivity of hexahydropyrroloquinolines

Stevenson, P., Hadden, M., Nieuwenhuyzen, M., Potts, D. & Thompson, N., 25 Jun 2001, In : Tetrahedron. 57(26), 26, p. 5615-5624 10 p.

Research output: Contribution to journalArticle

52 Citations (Scopus)

Synthesis of the heterocyclic core of the alkaloids martinelline and martinellic acid

Hadden, M., Nieuwenhuyzen, M., Osborne, D., Stevenson, P. & Thompson, N., 03 Sep 2001, In : Tetrahedron Letters, ISSN. 42, 36, p. 6417-6419 3 p.

Research output: Contribution to journalArticle

Stereochemistry
Imines
Cycloaddition
X ray crystallography
Cycloaddition Reaction
2000
33 Citations (Scopus)

Expedient synthesis of (+)-trans-5-allylhexahydroindolizidin-3-one

Potts, D., Stevenson, P. & Thompson, N., 08 Apr 2000, In : Tetrahedron Letters. 41, 2, p. 275-278 4 p.

Research output: Contribution to journalArticle

Alkaloids
Ions
Substrates
allyltrimethylsilane
22 Citations (Scopus)

Palladium catalysed formal 6-endo-trig approaches to pumiliotoxin alkaloids: interception of the elusive cyclopropyl intermediate

Feutren, S., McAlonan, H., Montgomery, D. & Stevenson, P., Nov 2000, In : Journal of the Chemical Society - Perkin Transactions 1. 7, 7, p. 1129-1137 9 p.

Research output: Contribution to journalArticle

Palladium
Alkaloids
Stereochemistry
Hydrides
Cyclization