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Synlett 1999; 1999(9): 1405-1406
DOI: 10.1055/s-1999-2868
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A Stereocontrolled Route to (-)-Epibatidine Using a Chiral cis-Cyclohexadiene-1,4-diol Equivalent

Hiromi Nakashima* , Kou Hiroya, Takahiko Taniguchi, Kunio Ogasawara
  • *Pharmaceutical Institute, Tohoku University, Aobayama, Sendai 980-8578, Japan; Fax + 81-22-2 17-68 45; E-mail: konol@mail.cc.tohoku.ac.jp
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Publication Date:
31 December 1999 (online)

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A concise diastereo- and enantio-controlled synthesis of (-)-epibatidine, the potent analgesic alkaloid from an Ecuadoran poison frog, Epipedobates tricolor, has been developed starting with a synthetic equivalent of chiral cis-cyclohexadiene-1,4-diol.

chiral building block - epibatidine - chiral cis-cyclohexadiene-1,4-diol - analgesic activity - frog poison alkaloid