Isolation, biosynthesis, and chemical syntheses of the hasubanan and acutumine alkaloids: A historical perspective

Creators: Grünenfelder, Denise C.; Reisman, Sarah E.¹; Navarro, Raul

1. California Institute of Technology

Abstract

The hasubanan and acutumine alkaloids comprise a large collection of aza-propellane natural products that possess varying degrees of structural complexity and biological activity. Since their initial structural elucidation in the 1960s, these alkaloids have garnered considerable attention from the synthetic community and have remained the subject of numerous studies aimed toward understanding their biosynthetic origins and synthesizing their complex architectures. Herein, we review the rich history associated with their isolation, characterization, biosynthetic origins, and chemical synthesis, with an emphasis on the range of synthetic strategies that have been implemented to access their aza-propellane framework. The unique features and history of each class of aza-propellanes are discussed in two separate sections of this account.

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Acknowledgement

Financial support was provided by the National Science Foundation (graduate research fellowship to D. C. G., Grant No. DGE-1144469, and CAREER-1057143, CHE-1800536, and CHE-2155163 to S. E. R.) and is gratefully acknowledged. R.N. acknowledges support from the American Chemical Society Petroleum Research Fund (59559-UNI1) and Occidental College.

Data Availability

No data was used for the research described in the article.

Conflict of Interest

The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper.

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