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Total synthesis of (−)-aritasone via the ultra-high pressure hetero-Diels–Alder dimerisation of (−)-pinocarvone (2017)
Journal Article
Uroos, M., Pitt, P., Harwood, L., Lewis, W., Blake, A. J., & Hayes, C. J. (in press). Total synthesis of (−)-aritasone via the ultra-high pressure hetero-Diels–Alder dimerisation of (−)-pinocarvone. Organic and Biomolecular Chemistry, 15(40), doi:10.1039/C7OB02204B. ISSN 1477-0520

This paper describes a total synthesis of the terpene-derived natural product aritasone via the hetero-Diels-Alder [4+2] cyclodimerisation of pinocarvove, which represents the proposed biosyntheic route. The hetero-Diels-Alder dimerisation of pinoca... Read More

Synthesis of triazole-linked morpholino oligonucleotides via Cu1 catalysed cycloaddition (2016)
Journal Article
Palframan, M. J., Alharthy, R. D., Powalowska, P. K., & Hayes, C. J. (in press). Synthesis of triazole-linked morpholino oligonucleotides via Cu1 catalysed cycloaddition. Organic and Biomolecular Chemistry, 14, doi:10.1039/C6OB00007J. ISSN 1477-0520

Triazole-linked morpholino (TLMO) oligonucleic acids were synthesised using the CuI catalysed (3 + 2) azide–alkyne cycloaddition (CuAAC) reaction. The modified DNA analogues were incorporated into 13-mer sequences via solid phase synthesis. UV meltin... Read More

Accessing low-oxidation state taxanes: is taxadiene-4(5)-epoxide on the taxol biosynthetic pathway? (2016)
Journal Article
Barton, N. A., Marsh, B. J., Lewis, W., Narraidoo, N., Seymour, G. B., Fray, R. G., & Hayes, C. J. (in press). Accessing low-oxidation state taxanes: is taxadiene-4(5)-epoxide on the taxol biosynthetic pathway?. Chemical Science, 7(5), doi:10.1039/c5sc03463a. ISSN 2041-6520

We have shown for the first time that taxadiene (3) can be epoxidised in a regio- and diastereoselective manner to provide taxadiene-4(5)-epoxide (12) as a single diastereoisomer, and that this epoxide can be rearranged to give taxa-4(20),11(12)-dien... Read More

Stereoselective synthesis of highly substituted tetrahydrofurans through diverted carbene O-H insertion reaction (2015)
Journal Article
Nicolle, S. M., Lewis, W., Hayes, C. J., & Moody, C. (2015). Stereoselective synthesis of highly substituted tetrahydrofurans through diverted carbene O-H insertion reaction. Angewandte Chemie International Edition, 54(29), 8485-8489. doi:10.1002/anie.201502484

Copper‐ or rhodium‐catalyzed reactions of diazocarbonyl compounds with β‐hydroxyketones give highly substituted tetrahydrofurans with excellent diastereoselectivity. Under mild conditions, the single‐step process starts as a carbene OH insertion rea... Read More

Stereoselective synthesis of highly substituted tetrahydrofurans by diverted carbene O–H insertion reaction (2015)
Journal Article
Nicolle, S. M., Lewis, W., Hayes, C. J., & Moody, C. J. (2015). Stereoselective synthesis of highly substituted tetrahydrofurans by diverted carbene O–H insertion reaction. Angewandte Chemie International Edition, 54(29), doi:10.1002/anie.201502484. ISSN 1433-7851

Copper or rhodium catalyzed reaction of diazocarbonyl compounds with β-hydroxyketones gives highly substituted tetrahydrofurans with excellent diastereoselectivity, under mild conditions, in a single step process that starts as a carbene O–H insertio... Read More