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

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 reduction

Publication 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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