690211-38-2Relevant academic research and scientific papers
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).
Application of intramolecular enyne metathesis to the synthesis of aza[4.2.1]bicyclics: Enantiospecific total synthesis of (+)-anatoxin-a
Brenneman, Jehrod B.,Martin, Stephen F.
, p. 1329 - 1331 (2007/10/03)
A concise synthesis of the potent nAChR agonist (4)-anatoxin-a (1) has been completed in a series of only nine chemical operations and 27% overall yield from commercially available D-methyl pyroglutamate (4). The synthesis features a novel procedure for t
