Journal of Organic Chemistry p. 2485 - 2487 (1986)
Update date:2022-08-04
Topics:
Wiseman, John R.
Lee, Susanna Y.
A short efficient synthesis of (+/-)-anatoxin-a, the alkaloidal toxin from Anabaena flos-aquae, is described.Bromination of 9-methyl-9-azabicyclo<3.3.1>nonan-1-ol (3b) provides the key intermediate 9-methyl-9-azabicyclo<4.2.1>nonan-2-one (6).Reaction of 6 with diethyl (1-cyanoethyl)phosphonate gives 2-(1-cyano-1-ethylidene)-9-methyl-9-azabicyclo<4.2.1>nonane (8).Oxygenation of 8, followed by reduction and hydrolysis, gives N-methylanatoxin-a (1b) which has been earlier converted into anatoxin-a.
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