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RESEARCH ARTICLE (Open Access)
Contents Vol 75(11)

My 37 years of working with nitrogen heterocycles and alkaloids

Stephen G. Pyne https://orcid.org/0000-0003-0462-0277 A *
+ Author Affiliations
- Author Affiliations

A School of Chemistry and Molecular Bioscience, University of Wollongong, Wollongong, NSW 2522, Australia.

* Correspondence to: spyne@uow.edu.au

Handling Editor: Curt Wentrup

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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[45]  S Umsumarng, P Pitchakarn, K Sastraruji, S Yodkeeree, AT Ung, SG Pyne, P Limtrakul, Reversal of human multi-drug resistance leukaemic cells by stemofoline derivatives via inhibition of P-glycoprotein function. Basic Clin Pharmacol Toxicol 2015, 116, 390.
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[67]  AW Carroll, SG Pyne, The history of the glycosidase inhibiting hyacinthacine C-type alkaloids: from discovery to synthesis. Curr Org Syn 2019, 16, 498.
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[74]  RK Chambers, N Chaipukdee, T Thaima, K Kanokmedhakul, SG Pyne, Synthesis of α-propargylglycinates using the Borono–Mannich reaction with pinacol allenylboronate and potassium allenyltrifluoroborate. Eur J Org Chem 2016, 2016, 3765.
         | Synthesis of α-propargylglycinates using the Borono–Mannich reaction with pinacol allenylboronate and potassium allenyltrifluoroborate.Crossref | GoogleScholarGoogle Scholar |

[75]  LM Joyce, MA Drew, AJ Tague, T Thaima, A Gouranourimi, A Ariafard, SG Pyne, CJT Hyland, A rare Alder-ene cycloisomerization of 1,6-allenynes. Chem Eur J 2022, 28, e202104022.
         | A rare Alder-ene cycloisomerization of 1,6-allenynes.Crossref | GoogleScholarGoogle Scholar |

[76]  F Zamani, SG Pyne, CJT Hyland, Oxazolidinones and 2,5-dihydrofurans via zinc-catalyzed regioselective allenylation reactions of l-α-amino aldehydes. J Org Chem 2017, 82, 6819.
         | Oxazolidinones and 2,5-dihydrofurans via zinc-catalyzed regioselective allenylation reactions of l-α-amino aldehydes.Crossref | GoogleScholarGoogle Scholar |

[77]  F Zamani, R Babaahmadi, BF Yates, MG Gardiner, A Ariafard, SG Pyne, CJT Hyland, Dual gold-catalyzed cycloaromatization of unconjugated (E)-enediynes. Angew Chem Int Ed 2019, 58, 2114.
         | Dual gold-catalyzed cycloaromatization of unconjugated (E)-enediynes.Crossref | GoogleScholarGoogle Scholar |

[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.
         | Rhodium-catalysed tetradehydro-Diels–Alder reactions of enediynes via a rhodium-stabilized cyclic allene.Crossref | GoogleScholarGoogle Scholar |

[79]  QH Pham, AJ Tague, C Richardson, CJT Hyland, SG Pyne, The Pd-catalysed asymmetric allylic alkylation reactions of sulfamidate imines. Chem Sci 2021, 12, 12695.
         | The Pd-catalysed asymmetric allylic alkylation reactions of sulfamidate imines.Crossref | GoogleScholarGoogle Scholar |

[80]  NK Swamy, A Yazici, SG Pyne, Copper-mediated cyclization−halogenation and cyclization−cyanation reactions of β-hydroxyalkynes and o-alkynylphenols and anilines. J Org Chem 2010, 75, 3412.
         | Copper-mediated cyclization−halogenation and cyclization−cyanation reactions of β-hydroxyalkynes and o-alkynylphenols and anilines.Crossref | GoogleScholarGoogle Scholar |

[81]  JC Jury, NK Swamy, A Yazici, AC Willis, SG Pyne, 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. J Org Chem 2009, 74, 5523.
         | 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 |

[82]  PJ Chevis, S Wangngae, T Thaima, AW Carroll, AC Willis, M Pattarawarapan, SG Pyne, Highly diastereoselective synthesis of enantioenriched anti-α-allyl-β-fluoroamines. Chem Commun 2019, 55, 6050.
         | Highly diastereoselective synthesis of enantioenriched anti-α-allyl-β-fluoroamines.Crossref | GoogleScholarGoogle Scholar |

[83]  PJ Chevis, T Promchai, C Richardson, T Limtharakul, SG Pyne, Synthesis of syn- and enantioenriched anti-β-amino alcohols by highly diastereoselective Borono–Mannich allylation reactions. Chem Commun 2022, 58, 2220.
         | Synthesis of syn- and enantioenriched anti-β-amino alcohols by highly diastereoselective Borono–Mannich allylation reactions.Crossref | GoogleScholarGoogle Scholar |

[84]  A Yazici, SG Pyne, 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. Org Lett 2013, 15, 5878.
         | 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 |

[85]  A Yazici, U Wille, SG Pyne, Synthesis of bridged heterocycles via sequential 1,4- and 1,2-addition reactions to α,β-unsaturated N-acyliminium ions: mechanistic and computational studies. J Org Chem 2016, 81, 1434.
         | 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 |

[86]  T Thaima, A Yazici, C Auranwiwat, AC Willis, U Wille, T Limtharakul, SG Pyne, Synthesis of spirocyclic heterocycles from α,β-unsaturated N-acyliminium ions. Org Biomol Chem 2021, 19, 259.
         | Synthesis of spirocyclic heterocycles from α,β-unsaturated N-acyliminium ions.Crossref | GoogleScholarGoogle Scholar |

[87]  GM Ryder, U Wille, AC Willis, SG Pyne, 1,2-Addition versus homoconjugate addition reactions of indoles and electron-rich arenes to α-cyclopropyl N-acyliminium ions: synthetic and computational studies. Org Biol Chem 2019, 17, 7025.
         | 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 |

[88]  IR Morgan, A Yazici, SG Pyne, BW Skelton, 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. J Org Chem 2008, 73, 2943.
         | 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 |

[89]  SG Pyne, B Dikic, PA Gordon, BW Skelton, AH White, Highly exo-diastereoselective Diels–Alder reactions of (2S)-N-benzoyl-2-tert-butyl-4-methylene-1,3-oxazolidin-5-one. J Chem Soc Chem Commun 1991, 1991, 1505.
         | Highly exo-diastereoselective Diels–Alder reactions of (2S)-N-benzoyl-2-tert-butyl-4-methylene-1,3-oxazolidin-5-one.Crossref | GoogleScholarGoogle Scholar |

[90]  SG Pyne, B Dikic, P Gordon, BW Skelton, AH White, Asymmetric\ synthesis of chiral cyclic amino acids by Diels–Alder reactions of (2S)- and (2R)-4-methyleneoxazolidin-5-ones. Aust J Chem 1993, 46, 73.
         | Asymmetric\ synthesis of chiral cyclic amino acids by Diels–Alder reactions of (2S)- and (2R)-4-methyleneoxazolidin-5-ones.Crossref | GoogleScholarGoogle Scholar |

[91]  SG Pyne, K Schafer, BW Skelton, AH White, Synthesis of novel conformationally restricted L-glutamate analogues. Chem Commun 1997, 1997, 2267.
         | Synthesis of novel conformationally restricted L-glutamate analogues.Crossref | GoogleScholarGoogle Scholar |

[92]  AT Ung, K Schafer, KB Lindsay, SG Pyne, K Amornraksa, R Wouters, I Van der Linden, I Biesmans, ASJ Lesage, BW Skelton, AH White, Synthesis and biological activities of conformationally restricted cyclopentenyl–glutamate analogues. J Org Chem 2002, 67, 227.
         | Synthesis and biological activities of conformationally restricted cyclopentenyl–glutamate analogues.Crossref | GoogleScholarGoogle Scholar |

[93]  AT Ung, SG Pyne, U Batenburg-Nguyen, AS Davis, A Sherif, F Bischoff, ASJ Lesage, Synthesis and antagonist activities of 4-aryl-substituted conformationally restricted cyclopentenyl and cyclopentanyl–glutamate analogues. Tetrahedron 2005, 61, 1803.
         | Synthesis and antagonist activities of 4-aryl-substituted conformationally restricted cyclopentenyl and cyclopentanyl–glutamate analogues.Crossref | GoogleScholarGoogle Scholar |

[94]  TQ Pham, SG Pyne, BW Skelton, AH White, Synthesis of carbocyclic hydantocidins via regioselective and diastereoselective phosphine-catalyzed [3 + 2]-cycloadditions to 5-methylenehydantoins. J Org Chem 2005, 70, 6369.
         | Synthesis of carbocyclic hydantocidins via regioselective and diastereoselective phosphine-catalyzed [3 + 2]-cycloadditions to 5-methylenehydantoins.Crossref | GoogleScholarGoogle Scholar |

[95]  SR Yong, MC Williams, SG Pyne, AT Ung, BW Skelton, AH White, P Turner, Synthesis of 2-azaspiro[4.4]nonan-1-ones via phosphine-catalysed [3+2]-cycloadditions. Tetrahedron 2005, 61, 8120.
         | Synthesis of 2-azaspiro[4.4]nonan-1-ones via phosphine-catalysed [3+2]-cycloadditions.Crossref | GoogleScholarGoogle Scholar |

[96]  SG Pyne, A Javidan, BW Skelton, AH White, Asymmetric synthesis of proline derivatives from (2R) and (2S)-2-tert-butyl-3-benzoyl-4-methyleneoxazolidin-5-one. Tetrahedron 1995, 51, 5157.
         | Asymmetric synthesis of proline derivatives from (2R) and (2S)-2-tert-butyl-3-benzoyl-4-methyleneoxazolidin-5-one.Crossref | GoogleScholarGoogle Scholar |

[97]  SG Pyne, J Safaei-G, F Koller, Exo-Diastereoselective 1,3-dipolar cycloadditions of azomethine ylides to (2R)-3-Benzoyl-4-methylene-2-phenyloxazolidin-5-one. Tetrahedron Lett 1995, 36, 2511.
         | Exo-Diastereoselective 1,3-dipolar cycloadditions of azomethine ylides to (2R)-3-Benzoyl-4-methylene-2-phenyloxazolidin-5-one.Crossref | GoogleScholarGoogle Scholar |

[98]  SG Pyne, J Safaei-G, BW Skelton, AH White, 1,3-Dipolar cycloadditions of a chiral oxazolidinone with nitrones and nitrile oxides. Aust J Chem 1995, 48, 1511.
         | 1,3-Dipolar cycloadditions of a chiral oxazolidinone with nitrones and nitrile oxides.Crossref | GoogleScholarGoogle Scholar |

[99]  SG Pyne, K Schafer, Diastereoselective addition of α-hydroxyalkyl and α-alkoxyalkyl radicals to chiral 4-methyleneoxazolidin-5-ones. Tetrahedron 1998, 54, 5709.
         | Diastereoselective addition of α-hydroxyalkyl and α-alkoxyalkyl radicals to chiral 4-methyleneoxazolidin-5-ones.Crossref | GoogleScholarGoogle Scholar |

[100]  GE Ball, GA Burley, L Chaker, BC Hawkins, JR Williams, PA Keller, SG Pyne, Structural reassignment of the mono- and bis-addition products from the addition reactions of N-(diphenylmethylene)glycinate esters to [60]fullerene under Bingel conditions. J Org Chem 2005, 70, 8572.
         | 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 |

[101]  R Thayumanavan, BC Hawkins, PA Keller, SG Pyne, GE Ball, A mild and general method for the synthesis of 5-substituted and 5,5-disubstituted fulleroprolines. Org Lett 2008, 10, 1315.
         | A mild and general method for the synthesis of 5-substituted and 5,5-disubstituted fulleroprolines.Crossref | GoogleScholarGoogle Scholar |

[102]  TE Shubina, DI Sharapa, C Schubert, D Zahn, M Halik, PA Keller, SG Pyne, S Jennepalli, DM Guldi, T Clark, Fullerene Van der Waals oligomers as electron traps. J Am Chem Soc 2014, 136, 10890.
         | Fullerene Van der Waals oligomers as electron traps.Crossref | GoogleScholarGoogle Scholar |

[103]  W Jaidee, RJ Andersen, BO Patrick, SG Pyne, C Muanprasate, S Borwornpinyo, S Laphookhieo, Alkaloids and styryllactones from Goniothalamus cheliensis. Phytochemistry 2019, 157, 8.
         | Alkaloids and styryllactones from Goniothalamus cheliensis.Crossref | GoogleScholarGoogle Scholar |

[104]  T Promchai, A Jaidee, S Cheenpracha, K Trisuwan, R Rattanajak, S Kamchonwongpaisan, S Laphookhieo, SG Pyne, T Ritthiwigrom, Antimalarial oxoprotoberberine alkaloids from the leaves of Miliusa cuneata. J Nat Prod 2016, 79, 978.
         | Antimalarial oxoprotoberberine alkaloids from the leaves of Miliusa cuneata.Crossref | GoogleScholarGoogle Scholar |

[105]  RA Ramli, W Lie, SG Pyne, Alkaloids from the roots of Stichoneuron caudatum and their acetylcholinesterase inhibitory activities. J Nat Prod 2014, 77, 894.
         | Alkaloids from the roots of Stichoneuron caudatum and their acetylcholinesterase inhibitory activities.Crossref | GoogleScholarGoogle Scholar |

[106]  P Wangchuk, PA Keller, SG Pyne, AC Willis, S Kamchonwongpaisan, Antimalarial alkaloids from a Bhutanese traditional medicinal plant Corydalis dubia. J Ethnopharm 2012, 143, 310.

[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 |

[108]  XD Dau, AC Willis, SG Pyne, Diastereoselective synthesis of the A-B-C tricyclic ring structure of stemocurtisine. Eur J Org Chem 2015, 2015, 7682.
         | Diastereoselective synthesis of the A-B-C tricyclic ring structure of stemocurtisine.Crossref | GoogleScholarGoogle Scholar |

[109]  P Wangchuk, S Navarro, C Shepherd, PA Keller, SG Pyne, A Loukas, Diterpenoid alkaloids of Aconitum laciniatum and mitigation of inflammation by 14-O-acetylneoline in a murine model of ulcerative colitis. Sci Rep 2015, 5, 12845.2015
         | Diterpenoid alkaloids of Aconitum laciniatum and mitigation of inflammation by 14-O-acetylneoline in a murine model of ulcerative colitis.Crossref | GoogleScholarGoogle Scholar |

[110]  CJ Dawurung, R Noitem, R Rattanajak, R Bunyong, C Richardson, AC Willis, S Kamchonwongpaisan, C Yimnual, C Muanprasat, SG Pyne, Isolation of CFTR and TMEM16A inhibitors from Neorautanenia mitis (A. Rich) Verdcourt: potential lead compounds for treatment of secretory diarrhea. Phytochemistry 2020, 179, 112464.
         | Isolation of CFTR and TMEM16A inhibitors from Neorautanenia mitis (A. Rich) Verdcourt: potential lead compounds for treatment of secretory diarrhea.Crossref | GoogleScholarGoogle Scholar |