Synthesis of Bicyclic Hydroxy Lactone Intermediates toward (-)-Tetrodotoxin

1 June 1995

journal article
letter
Published by Georg Thieme Verlag KG in Synlett

Vol. 1995 (SI) , 505-506
https://doi.org/10.1055/s-1995-5269

Abstract

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.

Keywords

TETRODOTOXIN
Α-HYDROXY LACTONE
RUTHENIUM OXIDATION
ZINC COPPER REDUCTION
EPOXIDE OPENING

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