Stephen G. Pyne

ORCID: 0000-0003-0462-0277
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Research Areas
  • Crystallization and Solubility Studies
  • X-ray Diffraction in Crystallography
  • Asymmetric Synthesis and Catalysis
  • Chemical synthesis and alkaloids
  • Chemical Synthesis and Analysis
  • Synthetic Organic Chemistry Methods
  • Advanced Synthetic Organic Chemistry
  • Synthesis and Catalytic Reactions
  • Carbohydrate Chemistry and Synthesis
  • Catalytic C–H Functionalization Methods
  • Traditional and Medicinal Uses of Annonaceae
  • Cyclopropane Reaction Mechanisms
  • Alkaloids: synthesis and pharmacology
  • Phytochemistry and Biological Activities
  • Natural product bioactivities and synthesis
  • Fullerene Chemistry and Applications
  • Crystallography and molecular interactions
  • Essential Oils and Antimicrobial Activity
  • Coordination Chemistry and Organometallics
  • Asymmetric Hydrogenation and Catalysis
  • Oxidative Organic Chemistry Reactions
  • Synthesis of Organic Compounds
  • Marine Sponges and Natural Products
  • Antimicrobial Peptides and Activities
  • Synthesis and Properties of Aromatic Compounds

University of Wollongong
2015-2024

Sustainable Horizons Institute
2019-2020

Illawarra Health and Medical Research Institute
2020

University of Kashan
2016

Silpakorn University
2014

Chiang Mai University
2003-2013

University of Technology Sydney
2010

Creative Commons
2009

Mahasarakham University
2009

The University of Western Australia
2001-2008

A range of substituted N-alkylisatins were synthesized and their cytotoxicity evaluated against several cancer cell lines in vitro. SAR studies indicated that the introduction an aromatic ring with a one or three carbon atom linker at N1 enhanced activity from allyl, 2'-methoxyethyl, 3'-methylbutyl N-substituted isatins. Furthermore, electron-withdrawing groups meta para position favored over ortho orientation. Of 24 compounds screened, nine displayed sub-micromolar IC50 values general...

10.1021/jm0704189 article EN Journal of Medicinal Chemistry 2007-09-21

This account describes our recent studies on the development of a general method preparing polyfunctionalized pyrrolidine, indolizidine, pyrrolizidine and pyrrolo[1,2-a]azepines their related alkaloids.

10.1055/s-2004-834801 article EN Synlett 2004-10-20

10.1016/s0040-4039(01)99801-6 article EN Tetrahedron Letters 1983-01-01

Aconitum laciniatum is used in Bhutanese traditional medicine for treating various chronic infections and inflammatory conditions. We carried out in-depth isolation characterization of the phytochemicals from root component determined anti-inflammatory effects isolated compounds against chemically-induced colitis mice. Five diterpenoid alkaloids - pseudaconitine, 14-veratroylpseudaconine, 14-O-acetylneoline, neoline, senbusine A were A. first time. Two tested properties TNBS-induced model...

10.1038/srep12845 article EN cc-by Scientific Reports 2015-08-04

Chiral α-hydroxy aldehydes generated in situ by the ADH reaction of vinyl sulfones undergo a borono-Mannich with β-styrenyl boronic acid and primary amines to give anti-1,2-amino alcohols high enantiomeric purities (83−95% ee). This new method allows much more rapid access these valuable chiral building blocks that has been used short formal synthesis (10 synthetic steps from 4-penten-1-ol) (−)-swainsonine.

10.1021/jo0610661 article EN The Journal of Organic Chemistry 2006-07-29

The asymmetric synthesis of (−)-swainsonine via a nonchiral pool route that involves the Sharpless epoxidation to induce chirality is reported. key steps involve vinyl epoxide aminolysis, ring-closing metathesis, and intramolecular N-alkylation prepare indolizidine ring highly diastereoselective cis-dihydroxylation using AD-mix-α. This synthetic strategy also allowed for (+)-1,2-di-epi-swainsonine (+)-1,2,8-tri-epi-swainsonine.

10.1021/jo025977w article EN The Journal of Organic Chemistry 2002-09-28

The generation of sulfidopeptide leukotrienes and leukotriene B (LTB) in response to an IgG-mediated immune complex reaction the peritoneal cavities rats fed either a menhaden oil-supplemented diet or beef tallow-supplemented for 9 10 wk was determined with combined techniques radioimmunoassay (RIA) reverse-phase high performance liquid chromatography. Rats on fish fat (FFD) incorporated eicosapentaenoic acid (EPA) into pulmonary splenic tissues EPA:arachidonic ratio approximately 2:1,...

10.4049/jimmunol.132.5.2559 article EN The Journal of Immunology 1984-05-01

The phosphine-catalyzed [3 + 2]-cycloaddition of 5-methylenehydantoins 4 with the ylides 5, derived from addition tributylphosphine to 2-butynoic acid derivatives, 6a−d, gives spiro-heterocyclic products. camphor sultam derivative 6b optically active Noteable was that ethyl 2-butynoate and 3-(2-butynoyl)-1,3-oxazolidin-2-one derivatives 6c 6d gave products reverse regioselectivities. N,N-dibenzylprotected cycloadduct has been converted carbocyclic hydantocidin 6,7-diepi-carbocyclic hydantocidin.

10.1021/jo050827h article EN The Journal of Organic Chemistry 2005-07-14

A flexible method for the diastereoselective total synthesis of pyrrolizidine alkaloids uniflorine A, casuarine, australine, and 3-epi-australine unnatural epimer 3,7-di-epi-australine from a common chiral 2,5-dihydropyrrole precursor is described.

10.1021/jo902355p article EN The Journal of Organic Chemistry 2009-12-22

The CuX (X = I, Br, Cl, CN)-mediated cyclization−halogenation and cyclization−cyanation reactions of β-hydroxyalkynes o-alkynylphenol -aniline derivatives give rise to 3-halo- 3-cyanofuro[3,2-b]pyrroles, 3-iodo-, 3-bromo-, 3-cyanobenzofurans, 3-cyanoindoles, respectively.

10.1021/jo1005119 article EN The Journal of Organic Chemistry 2010-04-21

This paper reviews the latest developments in synthesis of swainsonine and its analogues since first review this area by Nemr which covered literature up to 1999 (Nemr, A. E. Tetrahedron 2000, 56, 8579- 8629). Keywords: swainsonine, ring-closing metathesis, ruthenium catalysed rearrangement, epoxide, dihydroxylation, indolizine, pyrrolidine, meso compounds, asymmetric desymmetrization, enzyme kinetic resolution

10.2174/1570179052996900 article EN Current Organic Synthesis 2005-01-01

A diastereoselective synthesis of the putative structure natural product uniflorine has been achieved by using Petasis borono−Mannich reaction and ring-closing metathesis as key steps. The NMR data synthetic material did not match that reported for product. final was unequivocally determined single-crystal X-ray study its pentaacetate derivative. Thus it concluded proposed is incorrect.

10.1021/jo049806y article EN The Journal of Organic Chemistry 2004-04-01

ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTChiral sulfur compounds. 9. Stereochemistry of the intermolecular and intramolecular conjugate additions amines anions to chiral (E)- (Z)-vinyl sulfoxides. Total syntheses (R)-(+)-carnegine (+)- (-)-sedamineStephen G. Pyne, Peter Bloem, Sandra L. Chapman, Christine E. Dixon, Renate GriffithCite this: J. Org. Chem. 1990, 55, 3, 1086–1093Publication Date (Print):February 1, 1990Publication History Published online1 May 2002Published inissue 1...

10.1021/jo00290a051 article EN The Journal of Organic Chemistry 1990-02-01

The total synthesis of (+)-uniflorine A has allowed for the structural reassignment and configurational assignment alkaloid (−)-uniflorine from a 1,2,6,7,8-pentahydroxyindolizidine structure to (−)-(1R,2R,3R,6R,7S,7aR)-1,2,6,7-tetrahydroxy-3-hydroxymethylpyrrolizidine (6-epi-casuarine).

10.1021/ol8009144 article EN Organic Letters 2008-06-03

Superbugs stalled! Two newly designed synthetic dicationic peptoids (see one example; red O, blue N, green Cl) show promising in vitro bactericidal activity against a range of Gram-positive pathogens, including organisms resistant to vancomycin, methicillin, and linezolid, with only slow development resistance. Moreover their potency is maintained vivo. Detailed facts importance specialist readers are published as "Supporting Information". Such documents peer-reviewed, but not copy-edited or...

10.1002/anie.200904392 article EN Angewandte Chemie International Edition 2009-12-11

Density functional theory calculations indicate that van der Waals fullerene dimers and larger oligomers can form interstitial electron traps in which the electrons are even more strongly bound than isolated radical anions. The fullerenes behave like "super atoms", represent one-electron intermolecular σ-bonds. Spectroelectrochemical measurements on a bis-fullerene-substituted peptide provide experimental support. proposed deep relevant for all organic electronics applications non-covalently...

10.1021/ja505949m article EN Journal of the American Chemical Society 2014-07-22

The first phytochemical investigation of the stem extract Millettia extensa resulted in isolation and identification six new isoflavones, millexatins A–F (1–6), together with 16 known compounds. structures these compounds were determined on basis their spectroscopic data. Millexatin A (1) is a rare isoflavone containing three isoprenyl units modified ring. Compounds 1, 6, 10, 11, 14 displayed promising antibacterial activity MIC values 2–8 μg/mL.

10.1021/acs.jnatprod.8b00321 article EN Journal of Natural Products 2018-08-14
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