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Australian Journal of Chemistry Australian Journal of Chemistry Society
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Australian Journal of Chemistry

Australian Journal of Chemistry

Volume 76 Number 1 2023

Special Issue

9th Heron Island Conference

Guest Editor:
Curt Wentrup (School of Chemistry and Molecular Biosciences, The University of Queensland)

This collection of invited papers illustrates the wide variety of subjects discussed at the 9th Heron Island Conference, organised by Curt Wentrup and Craig Williams, held 26 June–2 July 2022 at the Heron Island Resort, Great Barrier Reef, Australia.

Graphical Abstract Image

N-Acyloxy-N-alkoxyamides are direct-acting mutagenic anomeric amides that react with DNA. Mutagenic activities reflect how structural elements impact on this interaction with DNA. Reliable QSARs (quantitative structure–activity relationships) reveal how hydrophobicity, reactivity and steric factors affect mutagenic activity and can discern intercalative ability of polycyclic aromatics, with good predictive ability.

CH22168Aryl/aryl diazoalkanes in rhodium(II)-catalyzed rearrangements of sulfur ylides

Lennard Kloene 0000-0002-9587-9219, Sripati Jana, Claire Empel and Rene M. Koenigs 0000-0003-0247-4384
pp. 25-29
Graphical Abstract Image

Detailed studies on aryl/aryl diazoalkanes are still underrepresented in organic synthesis. Herein, we report on rhodium-catalyzed [2,3]-sigmatropic rearrangement reactions of such diazoalkanes to further broaden the applicability of aryl/aryl diazoalkanes for the construction of densely functionalized small molecules.

CH22158Synthesis of a Gal-β-(1→4)-Gal disaccharide as a ligand for the fimbrial adhesin UcaD

Eric D. Boittier, Norbert Wimmer, Alexandria K. Harris, Mark A. Schembri and Vito Ferro 0000-0003-3306-2550
pp. 30-36
Graphical Abstract Image

Gal-β-(1→4)-Gal is a ligand for the adhesin UcaD, a fimbrial protein used by the Gram-negative pathogen Proteus mirabilis to infect the urinary tract. This disaccharide was prepared via glycosylation of a d-galactoside acceptor with a d-Gal trichloroacetimidate donor. The use of a thiogalactoside acceptor resulted in aglycone transfer side reactions.

CH22182Gold extraction using novel ionic thiourea derivatives

Megan L. Himmelman, Amir Joorab-Doozha, Christa L. Brosseau and Robert D. Singer 0000-0002-2708-9485
pp. 37-43
Graphical Abstract Image

The synthesis of novel ionic thiourea derivatives for use in gold extractions directed at exploiting the combined advantages of ionic liquids and thiourea while providing a greener alternative to cyanidation for the extraction of gold is reported. The ability to recycle the ionic thiourea derivatives while increasing their gold extraction efficiency has been targeted.

CH22200The ascidian Lissoclinum patella, the patellamides and copper

Philipp Baur, Peter Comba 0000-0001-7796-3532, Lawrence R. Gahan and Christian Scholz
pp. 44-48
Graphical Abstract Image

There are large quantities of cyclic peptides in Lissoclinum patella ascidians, produced by the obligate symbiont Prochloron. Ascidians accumulate copper but the generally assumed factor of 104 is much overestimated, and it is shown here that there is a significant accumulation factor >500 and up to approximately 3000.

Graphical Abstract Image

While gas-phase studies suggest that both palladium-mediated extrusion–insertion (ExIn) and condensation reactions operate for the generation of a N-phenyl-benzamide anion from the phenylsulfinate anion, a double desulfinative biaryl homocoupling reaction is favoured in the solution phase.

Graphical Abstract Image

This work describes the development of a new non‐metal Brønsted acid catalytic method for the synthesis of 2‐aryl‐3‐carboxylate ester furans and 2,3‐diaryl furans from ynone substrates. The method was shown to be efficient under very mild reaction conditions with up to 94% product yields. 

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