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Gustav Julius Wørmer

The [4.3.0] Piperidine Alkaloids: Architectures, Biology, Biosyntheses, and the Complete Details of the Asymmetric Syntheses of Streptazone A and Abikoviromycin

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Piperidine alkaloids continue to challenge the synthetic community by featuring densely functionalized scaffolds that often require careful chemical orchestration. Streptazone A and abikoviromycin are small and highly functionalized piperidine alkaloids, both accommodating Michael acceptors and a labile epoxide. These moieties are loaded into a [4.3.0] bicyclic core also present in other structurally related natural products, including the well-known piperidine alkaloid streptazolin. Here, we cover ring-closing strategies employed in earlier streptazolin syntheses; provide a concise overview of structures, biological properties, and biosyntheses of selected [4.3.0] piperidine alkaloids; and, finally, provide complete coverage of our recent asymmetric syntheses of streptazone A and abikoviromycin. 1 Introduction 2 Streptazolin Syntheses 3 Epo-[4.3.0] Piperidine Alkaloids 3.1 Streptazones 3.2 Abikoviromycin 3.3 Strepchazolin A and B 3.4 Hatomamicin 3.5 Kobutimycin A and B 3.6 Camporidines A and B 3.7 Epostatin 3.8 N-Hydroxydihydroabikoviromycin 3.9 Dihydroabikoviromycin 3.10 Biosynthesis of Streptazone E and Camporidines 4 Syntheses of the Streptazones and Abikoviromycin 4.1 Retrosynthesis 4.2 Results and Discussion 5 Conclusion.

OriginalsprogEngelsk
TidsskriftSynlett
Vol/bind32
Antal sider18
ISSN0936-5214
DOI
StatusUdgivet - 2021

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