1. Total synthesis of brevianamide A.
- Author
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Godfrey RC, Green NJ, Nichol GS, and Lawrence AL
- Subjects
- Alkaloids biosynthesis, Alkaloids chemistry, Biological Products chemistry, Cyclization, Molecular Structure, Penicillium metabolism, Piperazines chemistry, Spiro Compounds chemical synthesis, Spiro Compounds chemistry, Stereoisomerism, Alkaloids chemical synthesis, Biological Products chemical synthesis, Chemistry Techniques, Synthetic methods, Piperazines chemical synthesis
- Abstract
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, 750âmg scale), which involves a bioinspired cascade transformation of the linearly fused (-)-dehydrobrevianamide E into the topologically complex bridged-spiro-fused structure of (+)-brevianamide A.
- Published
- 2020
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