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Total synthesis of (±)-anatoxin-a via N-acyliminium intermediates

✍ Scribed by Karen H Melching; Henk Hiemstra; Wim J Klaver; W.Nico Speckamp

Publisher: Elsevier Science
Year: 1986
Tongue: French
Weight: 254 KB
Volume: 27
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(00)85068-6

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✦ Synopsis

Anatoxin-a has been synthesized in 8 steps, starting from succinimide, 4-bromo-l--butene and dimethyl (2-oxopropyl)phosphonate, by employing as the key step an intramolecular reaction of an N-acyliminium precursor with an cu,&unsaturated ketone moiety, induced by saturated HCl in MeOH at -5OOC.

Anatoxin-a (1) is a potent neurotoxin, produced by certain strains of the fresh water blue green alga Anabaena flos-aquae'. Both its unique structure (the only natural product identified to date with the 9-azabicyclo[4.2.1]nonane skeleton), and its significant biological properties (powerful nicotinic acetylcholine receptor agonist2) have aroused the interest of synthetic

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