Synthesis of anatoxin-a: very fast death factor

Abstract The synthesis of anatoxin-a ( 1 ) was completed by using the cycloaddition of 1-pyrroline 1-oxide ( 2 ) onto dienol ( 6 ), a reaction which proceeded with high stereoselectivity, regioselectivity, and site selectivity. The resultant adduct (i.e. 7 ) was oxidized to a second nitrone (i.e. 8 ) which undergoes a second closure to afford cycloadduct 9a with regiospecificity. The conversion of 9a into anatoxin-a hydrochloride ( 1 · HC1) was both direct and efficient.