Total synthesis of brevianamide A

Robert C. Godfrey, Nicholas J. Green, Gary S. Nichol, Andrew L. Lawrence

Research output: Contribution to journalArticlepeer-review

Abstract / Description of output

The fungal-derived bicyclo[2.2.2]diazaoctane alkaloids are of interest to the scientific community for their potent and varied biological activities. Within this large and diverse family of natural products, the insecticidal metabolite (+)-brevianamide A is particularly noteworthy for its synthetic intractability and inexplicable biogenesis. Despite five decades of research, this alkaloid has remained an elusive target for chemical synthesis due to insurmountable issues of reactivity and selectivity associated with all previously explored strategies. We herein report the chemical synthesis of (+)-brevianamide A (seven steps, 7.2% overall yield, 750 mg scale), which involves a bioinspired cascade transformation of the linearly fused (−)-dehydrobrevianamide E into the topologically complex bridged-spiro-fused structure of (+)-brevianamide A.
Original languageEnglish
Pages (from-to)615-619
Number of pages6
JournalNature Chemistry
Early online date13 Apr 2020
Publication statusPublished - Jul 2020


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