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Synlett 1998; 1998(4): 371-372
DOI: 10.1055/s-1998-1682
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Stereoelectronic and Steric Effects for Critical Oxidation to the Cyclohexane Derivatives for an Intermediate to (-)-Tetrodotoxin

Makoto Bamba* , Toshio Nishikawa, Minoru Isobe
  • *Laboratory of Organic Chemistry, School of Bioagricultural Sciences, Nagoya University, Chikusa, Nagoya 464-8601, Japan
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Publication Date:
31 December 2000 (online)

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A critical step for hydroxylation to cyclohexane ring at the 10 alpha orientation of an intermediate to tetrodotoxin was achieved through a limited precursor by allylic oxidation with SeO2. In all the cases stereocontrol was rendered by strictly stereoelectronic and steric effects to give exact products.

(-)-tetrodotoxin - hydroxylation - SeO2 - stereoelectronic effects - steric effects

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