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Issue 11, 2011
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A robust and scalable synthesis of the potent neuroprotective agent (−)-huperzine A

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Abstract

(−)-Huperzine A (1) is a tricyclic alkaloid that is produced in low yield by the Chinese herb Huperzia serrata. There is intense contemporary interest in clinical application of (−)-huperzine A (1) for treating neurodegenerative diseases and protecting against the lethal effects of chemical warfare agents, such as sarin and VX. We report a robust, scalable, and efficient synthesis of (−)-huperzine A (1) from (R)-4-methyl-cyclohex-2-ene-1-one (5). Our route proceeds in 35–45% overall yield, delivers (−)-huperzine A (1) in only eight steps from cyclohexenone 5, requires only three chromatographic purifications, and can provide gram quantities of the target. This route represents a critical, enabling advance toward detailed evaluation of (−)-huperzine A (1) in clinical settings.

Graphical abstract: A robust and scalable synthesis of the potent neuroprotective agent (−)-huperzine A

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Publication details

The article was received on 12 Jul 2011, accepted on 29 Jul 2011 and first published on 25 Aug 2011


Article type: Edge Article
DOI: 10.1039/C1SC00455G
Citation: Chem. Sci., 2011,2, 2251-2253
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    A robust and scalable synthesis of the potent neuroprotective agent (−)-huperzine A

    M. K. M. Tun, D. Wüstmann and S. B. Herzon, Chem. Sci., 2011, 2, 2251
    DOI: 10.1039/C1SC00455G

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