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Anatoxin a
("Very Fast Death Factor")
"Efficient Total Synthesis of (+/-)-Anatoxin a",
R. L. Danheiser, J. M. Morin, Jr., and E. J. Salaski, J.
Am. Chem. Soc. 1985,
107, 8066.
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Anatoxin a is a potent neurotoxic alkaloid isolated from
blue-green algae. It is one of the most potent agonists at the
nicotinic acetylcholine receptor discovered to date (visit the anatoxin
webpage). The pivotal step in our 1985 synthesis involves the
disrotatory electrocyclic cleavage - transannular cyclization of the
bicyclic amine A. An asymmetric version of our strategy has recently
been reported by Trost and Oslob (J.
Am. Chem. Soc. 1999, 121, 3057).
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