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Hill, Robert A.; Sutherland, Andrew

doi:10.1039/c4np90032d

Cited by 4 publications

(1 citation statement)

References 32 publications

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“…There is high biological and synthetic interest in many thiazole‐ and thiazoline‐containing natural products, such as thiangazole, [1] didehydromirabazole, [2] baringolin, [3] and apratoxin, [4] due to their striking tumor‐selective cytotoxicity, antibiotic and/or antiviral activities. The recently highlighted [5] thiamyxins represent a new group of thiazole/thiazoline‐rich natural products, isolated from a myxobacterial strain of the Myxococcaceae family (MCy9487) by Müller and co‐workers [6] …”

Section: Figurementioning

confidence: 99%

Total Synthesis of Thiamyxins A–C and Thiamyxin E, a Potent Class of RNA‐Virus‐Inhibiting (Cyclo)depsipeptides

Bauer

Kazmaier

2023

Angew Chem Int Ed

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We present the first total synthesis of the thiamyxins A–C and the now fully characterized thiamyxin E, an interesting class of thiazole‐ and thiazoline‐rich depsipeptides with diverse antiviral activity. The synthesis features a parallel closing of two methyl thiazoline units, with low epimerization of the very labile adjacent stereocenter. It also includes the three‐step synthesis of an uncommon hydroxy acid and the oxidation‐free elimination of a phenylselenide to form a dehydroalanine moiety. The exploitation of the acid‐labile stereocenter at the isoleucine moiety and the reopening of the macrolactones gave access to the four thiamyxins with good yields and diastereomeric purities from a single precursor. The modular total synthesis allows further testing of the biological activity and gives opportunities to explore the pharmacophore and antiviral target through derivatization.

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Section: Figurementioning

confidence: 99%

Total Synthesis of Thiamyxins A–C and Thiamyxin E, a Potent Class of RNA‐Virus‐Inhibiting (Cyclo)depsipeptides

Bauer

Kazmaier

2023

Angew Chem Int Ed

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Cytotoxic sesquiterpenes from the endophytic fungus Pseudolagarobasidium acaciicola

et al. 2016

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Alstoscholarisines H–J, Indole Alkaloids from Alstonia scholaris: Structural Evaluation and Bioinspired Synthesis of Alstoscholarisine H

et al. 2016

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Alstoscholarisines H-J (1-3), new monoterpenoid indole alkaloids with an unprecedented skeleton created via the formation of a C-3/N-1 bond, were isolated from Alstonia scholaris. Their structures were established by extensive spectroscopic analyses and the assessment of single-crystal X-ray diffraction data. The total synthesis of alstoscholarisine H was achieved via the regioselective nucleophilic addition of pyridinium through a bioinspired iminium ion intermediate followed by Pictet-Spengler-like cyclization.

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Hot off the press

Cited by 4 publications

References 32 publications

Total Synthesis of Thiamyxins A–C and Thiamyxin E, a Potent Class of RNA‐Virus‐Inhibiting (Cyclo)depsipeptides

Total Synthesis of Thiamyxins A–C and Thiamyxin E, a Potent Class of RNA‐Virus‐Inhibiting (Cyclo)depsipeptides

Cytotoxic sesquiterpenes from the endophytic fungus Pseudolagarobasidium acaciicola

Alstoscholarisines H–J, Indole Alkaloids from Alstonia scholaris: Structural Evaluation and Bioinspired Synthesis of Alstoscholarisine H

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