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Synlett 1997; 1997(SI): 447-448
DOI: 10.1055/s-1997-6142
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Synthesis of (±)-12-Fluorohuperzine A, a Novel Acetylcholinesterase Inhibitor

Satoru Kaneko, Mayumi Shikano, Tadashi Katoh, Shiro Terashima*
  • *Sagami Chemical Research Center, Nishi-Ohnuma, Sagamihara, Kanagawa 229, Japan
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Publication Date:
31 December 2000 (online)

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The synthesis of (±)-12-fluorohuperzine A (5) has been accomplished by a method featuring the regioselective formation of the allyl bromide 8 from the exo-olefin 7 (7→8), the masking of the allyl alcohol 16 in a form of the ethyl acrylate 19 (16→17→18→19), and the conversion of the allyl alcohol 21 to the allyl fluoride 5 (21→5) as key steps. Taking into account its racemic form, this analogue exhibits 20 times less potent anti-acetylcholinesterase activity than natural (-)-huperzine A (1).

(-)-huperzine A - (±)-12-fluorohuperzine A - acetylcholinesterase inhibitor - allyl bromide formation - monofluorination