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Survey of Tetrodotoxin
Syntheses
Steve Miller
SuperGroup Meeting
06/02/04
Outline
• Introduction and trivia
• Kishi synthesis (1972, racemic)
• Isobe synthesis (2003, asymmetric)
• Du Bois synthesis (2003, asymmetric)
• References
“Certain varieties of puffer fish, especially the
tora fugu,
or
tiger puffer
(S. rubripes),
and the closely related
ma fugu
, or
common puffer (
S. porphyreus
), are highly prized as
comestibles in Japan. The indulgence of the taste is fraught
with some peril, since the livers and ovaries of the fish contain
a powerful poison.”
R. B. Woodward
[“The Structure of Tetrodotoxin”
Pure & Appl
.
Chem
. 1964
,
9
, 49]
Introduction
• First isolated from the
ovaries of the puffer
fish (Fugu) in 1909.
• Named after the
puffer fish family
“Tetraodontidae.”
• Responsible for 10-
200 deaths per year.
Tetrodotoxin Trivia
• 1200 times deadlier than cyanide. One
fish contains enough poison to kill 30
adults.
• Must be licensed to prepare fugu. Typical
meal is $100-200. Some chefs add a
small amount of toxin to the meal for a
“tingly” effect.
• Supposedly the only delicacy not served
the Japanese emperor.
Trivia Continued
• Toxin is actually generated by the bacteria
Pseudomonas
which the fish consumes
• A potent neurotoxin, it binds to pores of Na-
channel proteins in nerve-cell membranes.
• It does not cross the blood-brain barrier,
rendering the victim fully conscious but
paralyzed. Death is typically from asphyxiation.
• No antidote. Treatment is emptying of the
stomach, consumption of activated charcoal,
and hoping for the best.
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