A transannular reaction was proposed to access the Lycopodium alkaloid lycopodine. A key bicyclic precursor was synthesized via a ring-closing metathesis reaction. Initial evaluations of the transannular aza-Prins reaction to synthesize lycopodine were reported and discussed.
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Extracted and adapted from the Master’s thesis of Michaela C. Vertorano, Synthetic study toward lycopodium alkaloids via a common bicyclic intermediate. University at Albany, State University of New York; 2016.
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This work is dedicated to Professor Samuel J. Danishefsky. Start-up funds from SUNY-Albany are greatly acknowledged. Zheng Wei thanks National Science Foundation (Award No. 1337594) for the X-ray diffractometer. We thank NSF for NMR and mass spectrometers (1726724 and 1429329, respectively). We thank Professors Ting Wang and Qiang Zhang, who were postdoctoral scholars in the Danishefsky group, for stimulating discussions. Dr. Ying Wu is thanked for helping in the preparation of this manuscript.
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Vertorano, M.C., Johnson, K.L., He, P. et al. A transannular approach toward lycopodine synthesis. J Antibiot 72, 494–497 (2019). https://doi.org/10.1038/s41429-019-0155-2