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A transannular approach toward lycopodine synthesis

The Journal of Antibiotics volume 72, pages 494–497 (2019)Cite this article

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Abstract

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.

In conclusion, an advanced intermediate 20 was synthesized in a straightforward way. This intermediate could potentially be useful in the synthesis of lycopodine via transannular cyclization strategies.

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Fig. 1
Scheme 1
Scheme 2
Scheme 3

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Acknowledgements

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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  1. Department of Chemistry, University at Albany, State University of New York, 1400 Washington Avenue, Albany, NY, 12222, USA

    Michaela C. Vertorano, Kyla L. Johnson, Ping He, Zheng Wei & Zhang Wang

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  1. Michaela C. Vertorano
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Correspondence to Zhang Wang.

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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

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