120692-41-3Relevant articles and documents
Enantioselective synthesis of (+)-anatoxin-a via enyne metathesis
Brenneman, Jehrod B.,Machauer, Rainer,Martin, Stephen F.
, p. 7301 - 7314 (2007/10/03)
A concise synthesis of the potent nAChR agonist (+)-anatoxin-a (1) has been completed by a series of nine chemical operations and in 27% overall yield from commercially available D-methyl pyroglutamate (12). The strategy featured the application of a new protocol for the diastereoselective synthesis of cis-2,5-disubstituted pyrrolidines bearing unsaturated side chains and an intramolecular enyne metathesis to provide the bridged bicyclic framework of 1. Thus, D-methyl pyroglutamate (12) was converted in five steps to 32, which underwent facile enyne metathesis to deliver the bicyclic diene 33. Selective oxidative cleavage of the less substituted carbon-carbon double bond in 33 followed by deprotection furnished (+)-anatoxin-a (1).
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.
