Tetrahedron

The use of nitrones in the synthesis of anatoxin-a, very fast death factor

JJ Tufariello, H Meckler, KPA Senaratne

Index: Tufariello; Meckler; Pushpananda; Senaratne Tetrahedron, 1985 , vol. 41, # 17 p. 3447 - 3453

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Citation Number: 59

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 (ie 7) was oxidized to a second nitrone (ie 8) which undergoes a second closure to afford cycloadduct 9a with regiospecificity. The conversion of 9a into anatoxin-a hydrochloride (1· HC1) was both ...