- Application of intramolecular enyne metathesis to the synthesis of aza[4.2.1]bicyclics: enantiospecific total synthesis of (+)-anatoxin-a.
Application of intramolecular enyne metathesis to the synthesis of aza[4.2.1]bicyclics: enantiospecific total synthesis of (+)-anatoxin-a.
Organic letters (2004-04-09)
Jehrod B Brenneman, Stephen F Martin
PMID15070329
RESUMO
A concise synthesis of the potent nAChR agonist (+)-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 the diastereoselective preparation of cis-2,5-disubstituted pyrrolidines leading to 10, which underwent an intramolecular enyne metathesis to afford a bridged azabicyclic intermediate that was transformed into 1. [reaction: see text]
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