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DOI: 10.1055/a-1688-0826
The [4.3.0] Piperidine Alkaloids: Architectures, Biology, Biosyntheses, and the Complete Details of the Asymmetric Syntheses of Streptazone A and Abikoviromycin
Novo Nordisk Foundation (NNF19OC0054782) to T.B.P.; Carlsberg foundation (CF17-0800) to T.B.P.
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Abstract
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
Key words
piperidine alkaloids - electrophilic natural products - total synthesis - asymmetric synthesis - Pauson–Khand cyclization - enaminone reductionPublication History
Received: 27 October 2021
Accepted after revision: 05 November 2021
Accepted Manuscript online:
05 November 2021
Article published online:
03 December 2021
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