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Gustav Julius Wørmer

Concise Asymmetric Syntheses of Streptazone A and Abikoviromycin**

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DOI

Streptazone A and abikoviromycin are alkaloids that both feature an unusual arrangement of reactive functionalities within a compact tricyclic ring system. Here, we report a highly concise asymmetric synthesis of both natural products. The route first constructs another family member, streptazone B1, using a rhodium-catalyzed distal selective allene-ynamide Pauson–Khand reaction. A regio- and enantioselective epoxidation under chiral phase-transfer catalytic conditions directly afforded streptazone A in 8 steps overall. In one additional step, a chemoselective, iridium-catalyzed reduction of the enaminone system then gave abikoviromycin. The reactivity of streptazone A towards a cysteine mimic, N-acetylcysteamine, was studied and revealed unanticipated transformations, including bis-thiol conjugation which may proceed via formation of a cyclopentadienone intermediate. With flexible access to these compounds, studies aimed to identify their direct biological targets are now possible.

OriginalsprogEngelsk
TidsskriftAngewandte Chemie - International Edition
Vol/bind60
Nummer19
Sider (fra-til)10521-10525
Antal sider5
ISSN1433-7851
DOI
StatusUdgivet - maj 2021

Bibliografisk note

Funding Information:
This work was supported by grants from the Novo Nordisk Foundation (grant NNF19OC0054782 to T.B.P.) and the Carlsberg Foundation (grant CF17‐0800 to T.B.P.). We further thank the K. A. Jørgensen lab for access to chiral stationary phase UPC and Anders Bodholt Nielsen and Dennis Wilkens Juhl for technical assistance with NMR spectroscopy. Lastly, we thank the Troels Skrydstrup lab for technical assistance using the two‐chamber system and Jens Christian Kondrup for scientific glassware design. 2

Funding Information:
This work was supported by grants from the Novo Nordisk Foundation (grant NNF19OC0054782 to T.B.P.) and the Carlsberg Foundation (grant CF17-0800 to T.B.P.). We further thank the K. A. J?rgensen lab for access to chiral stationary phase UPC2 and Anders Bodholt Nielsen and Dennis Wilkens Juhl for technical assistance with NMR spectroscopy. Lastly, we thank the Troels Skrydstrup lab for technical assistance using the two-chamber system and Jens Christian Kondrup for scientific glassware design.

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© 2021 Wiley-VCH GmbH

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