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.
Chirospecific Synthesis of Nitrogen and Side Chain Modified Analogues of (+)-Anatoxin
Sardina, F. Javier,Howard, Michael H.,Koskinen, Ari M. P.,Rapoport, Henry
, p. 4654 - 4660 (2007/10/02)
Improvements in the chirospecific synthesis of (+)-anatoxin from D-glutamic acid have resulted in a process that gives enantiomerically pure material in reproducible 25percent overall yield.The major synthetic modifications have been in the decarbonylative iminium ion cyclization and in the introduction of the enone moiety.With multigram quantities of (+)-anatoxin thus available, a series of nitrogen and side chain modified analogues have been prepared.These analogues were chosen to provide probes for the agonist-receptor interaction model of acetylcholine.They include secondary, tertiary, and quaternary nitrogen derivatives and those in which the carbonyl function has been converted to secondary and tertiary alcohol and ester functions.
