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Synlett 1995; 1995(SI): 505-506
DOI: 10.1055/s-1995-5269
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Synthesis of Bicyclic Hydroxy Lactone Intermediates toward (-)-Tetrodotoxin

Noboru Yamamoto, Toshio Nishikawa, Minoru Isobe*
  • *Laboratory of Organic Chemistry, School of Agricultural Sciences, Nagoya University, Chikusa, Nagoya 464-01, Japan
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Publication Date:
31 December 2000 (online)

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Tetrodotoxin has a characteristic orthoester (hemilactal) existing in equilibrium with the corresponding α-hydroxy lactone. This paper deals with efficient syntheses of 2 analogous hydroxy lactones. The first one includes trans-lactonization accompanied by opening of epoxide. The second synthesis ends up with oxidative cleavage of vinyl group with RuO4 as crucial step for this lactone.

tetrodotoxin - α-hydroxy lactone - ruthenium oxidation - zinc copper reduction - epoxide opening