My 37 years of working with nitrogen heterocycles and alkaloids
Stephen G. Pyne
A *
+ Author Affiliations
- Author Affiliations
A School of Chemistry and Molecular Bioscience, University of Wollongong, Wollongong, NSW 2522, Australia.
Australian Journal of Chemistry 75(11) 923-944 https://doi.org/10.1071/CH22144
Submitted: 23 June 2022 Accepted: 11 August 2022 Published: 10 November 2022
© 2022 The Author(s) (or their employer(s)). Published by CSIRO Publishing. This is an open access article distributed under the Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International License (CC BY-NC-ND)
Abstract
This account highlights work from my laboratory at the University of Wollongong (UOW), concerning nitrogen heterocycles and alkaloids, from my appointment as lecturer in Chemistry in February 1985 to the present time as an Emeritus Professor since 2022. I am thankful to the Royal Australian Chemical Institute for the recognition of my work through the recent award of a Distinguished Fellow at the national conference in Brisbane in July 2022.
Keywords: 1,2-amino alcohols, alkaloid, borono-Mannich reaction, cycloadditions, metal catalysis, structural corrections, sulfoxide, sulfoximine, vinyl epoxides.
References
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[78] S Thadkapally, K Farshadfar, MA Drew, C Richardson, A Ariafard, SG Pyne, CJT Hyland, Rhodium-catalysed tetradehydro-Diels–Alder reactions of enediynes via a rhodium-stabilized cyclic allene. Chem Sci 2020, 11, 10945.
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| Copper-mediated cyclization−halogenation and cyclization−cyanation reactions of β-hydroxyalkynes and o-alkynylphenols and anilines.Crossref | GoogleScholarGoogle Scholar |
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| Metal-catalyzed cycloisomerization reactions of cis-4-hydroxy-5-alkynylpyrrolidinones and cis-5-hydroxy-6-alkynylpiperidinones: synthesis of furo[3,2-b]pyrroles and furo[3,2-b]pyridines.Crossref | GoogleScholarGoogle Scholar |
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| Highly diastereoselective synthesis of enantioenriched anti-α-allyl-β-fluoroamines.Crossref | GoogleScholarGoogle Scholar |
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| Synthesis of syn- and enantioenriched anti-β-amino alcohols by highly diastereoselective Borono–Mannich allylation reactions.Crossref | GoogleScholarGoogle Scholar |
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| Sequential 1,4- and 1,2-addition reactions to α,β-unsaturated N-acyliminium ions: a new strategy for the synthesis of spiro and bridged heterocycles.Crossref | GoogleScholarGoogle Scholar |
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| Synthesis of bridged heterocycles via sequential 1,4- and 1,2-addition reactions to α,β-unsaturated N-acyliminium ions: mechanistic and computational studies.Crossref | GoogleScholarGoogle Scholar |
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| Synthesis of spirocyclic heterocycles from α,β-unsaturated N-acyliminium ions.Crossref | GoogleScholarGoogle Scholar |
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| 1,2-Addition versus homoconjugate addition reactions of indoles and electron-rich arenes to α-cyclopropyl N-acyliminium ions: synthetic and computational studies.Crossref | GoogleScholarGoogle Scholar |
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| Diastereoselective Ritter reactions of chiral cyclic N-acyliminium ions: synthesis of pyrido- and pyrrolo[2,3-d]oxazoles and 4-hydroxy-5-N-acylaminopyrrolidines and 5-hydroxy-6-N-acylaminopiperidines.Crossref | GoogleScholarGoogle Scholar |
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| Highly exo-diastereoselective Diels–Alder reactions of (2S)-N-benzoyl-2-tert-butyl-4-methylene-1,3-oxazolidin-5-one.Crossref | GoogleScholarGoogle Scholar |
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| Asymmetric\ synthesis of chiral cyclic amino acids by Diels–Alder reactions of (2S)- and (2R)-4-methyleneoxazolidin-5-ones.Crossref | GoogleScholarGoogle Scholar |
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| Synthesis of novel conformationally restricted L-glutamate analogues.Crossref | GoogleScholarGoogle Scholar |
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| Synthesis and biological activities of conformationally restricted cyclopentenyl–glutamate analogues.Crossref | GoogleScholarGoogle Scholar |
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| Synthesis and antagonist activities of 4-aryl-substituted conformationally restricted cyclopentenyl and cyclopentanyl–glutamate analogues.Crossref | GoogleScholarGoogle Scholar |
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| Synthesis of carbocyclic hydantocidins via regioselective and diastereoselective phosphine-catalyzed [3 + 2]-cycloadditions to 5-methylenehydantoins.Crossref | GoogleScholarGoogle Scholar |
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| Synthesis of 2-azaspiro[4.4]nonan-1-ones via phosphine-catalysed [3+2]-cycloadditions.Crossref | GoogleScholarGoogle Scholar |
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| Asymmetric synthesis of proline derivatives from (2R) and (2S)-2-tert-butyl-3-benzoyl-4-methyleneoxazolidin-5-one.Crossref | GoogleScholarGoogle Scholar |
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| Exo-Diastereoselective 1,3-dipolar cycloadditions of azomethine ylides to (2R)-3-Benzoyl-4-methylene-2-phenyloxazolidin-5-one.Crossref | GoogleScholarGoogle Scholar |
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| 1,3-Dipolar cycloadditions of a chiral oxazolidinone with nitrones and nitrile oxides.Crossref | GoogleScholarGoogle Scholar |
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| Diastereoselective addition of α-hydroxyalkyl and α-alkoxyalkyl radicals to chiral 4-methyleneoxazolidin-5-ones.Crossref | GoogleScholarGoogle Scholar |
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| Structural reassignment of the mono- and bis-addition products from the addition reactions of N-(diphenylmethylene)glycinate esters to [60]fullerene under Bingel conditions.Crossref | GoogleScholarGoogle Scholar |
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| A mild and general method for the synthesis of 5-substituted and 5,5-disubstituted fulleroprolines.Crossref | GoogleScholarGoogle Scholar |
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| Fullerene Van der Waals oligomers as electron traps.Crossref | GoogleScholarGoogle Scholar |
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| Alkaloids and styryllactones from Goniothalamus cheliensis.Crossref | GoogleScholarGoogle Scholar |
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| Antimalarial oxoprotoberberine alkaloids from the leaves of Miliusa cuneata.Crossref | GoogleScholarGoogle Scholar |
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| Alkaloids from the roots of Stichoneuron caudatum and their acetylcholinesterase inhibitory activities.Crossref | GoogleScholarGoogle Scholar |
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[107] CJ Dawurung, JG Gotep, JG Usman, IL Elisha, LH Lombin, SG Pyne, Antidiarrheal activity of some selected Nigerian plants used in traditional medicine. Pharmacogn Res 2019, 11, 371.
| Antidiarrheal activity of some selected Nigerian plants used in traditional medicine.Crossref | GoogleScholarGoogle Scholar |
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| Diastereoselective synthesis of the A-B-C tricyclic ring structure of stemocurtisine.Crossref | GoogleScholarGoogle Scholar |
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| Diterpenoid alkaloids of Aconitum laciniatum and mitigation of inflammation by 14-O-acetylneoline in a murine model of ulcerative colitis.Crossref | GoogleScholarGoogle Scholar |
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| Isolation of CFTR and TMEM16A inhibitors from Neorautanenia mitis (A. Rich) Verdcourt: potential lead compounds for treatment of secretory diarrhea.Crossref | GoogleScholarGoogle Scholar |
