Stereoselective and efficient total synthesis of optically active tetrodotoxin from D-glucose

The Journal of Organic Chemistry
Ken-ichi SatoJuji Yoshimura

Abstract

A stereoselective and efficient total synthesis of optically active tetrodotoxin (TTX) is described. A polyfunctionalized key cyclitol compound containing branched-chains for the synthesis of TTX was prepared from D-glucose employing the Henry reaction (Nitro aldol reaction) as the key transformation. Stereoselective construction of the alpha-azido-aldehyde branched-chain was achieved via the key spiro alpha-chloroepoxide intermediate.

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Nov 11, 2011·Marine Drugs·Jaclyn Chau, Marco A Ciufolini
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