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doi: 10.1021/ol401582e
pmid: 23834719
Conversion of a simple furan into the intact erythrinane skeleton in one synthetic operation has been accomplished. The one-pot reaction sequence begins with singlet oxygen photooxygenation of the furan and proceeds via a 2-pyrrolidinone formation, cyclization of the pendant aldehyde moiety and an N-acyliminium ion formation and terminates with a Pictet-Spengler-type aromatic substitution. The method has been used to achieve a rapid and highly effective formal synthesis of erysotramidine.
Pictet-Spengler, Molecular Structure, Singlet oxygen, Erysotramidine, Stereoisomerism, Heterocyclic Compounds, 4 or More Rings, Pyrrolidinones, Erythrina Alkaloids, Alkaloids, Cyclization, Furans, Erythrina
Pictet-Spengler, Molecular Structure, Singlet oxygen, Erysotramidine, Stereoisomerism, Heterocyclic Compounds, 4 or More Rings, Pyrrolidinones, Erythrina Alkaloids, Alkaloids, Cyclization, Furans, Erythrina
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