70470-06-3Relevant articles and documents
Synthesis of Anatoxin-a
Wiseman, John R.,Lee, Susanna Y.
, p. 2485 - 2487 (1986)
A short efficient synthesis of (+/-)-anatoxin-a, the alkaloidal toxin from Anabaena flos-aquae, is described.Bromination of 9-methyl-9-azabicyclononan-1-ol (3b) provides the key intermediate 9-methyl-9-azabicyclononan-2-one (6).Reaction of 6 with diethyl (1-cyanoethyl)phosphonate gives 2-(1-cyano-1-ethylidene)-9-methyl-9-azabicyclononane (8).Oxygenation of 8, followed by reduction and hydrolysis, gives N-methylanatoxin-a (1b) which has been earlier converted into anatoxin-a.