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Step synthesis of the erythrinane skeleton by acid promoted double cyclization of n cyclohex 1 enyl n 2 3 4 dimethoxyphenylethyl alpha methylsulfinylacetamide and its derivatives


, : Step synthesis of the erythrinane skeleton by acid promoted double cyclization of n cyclohex 1 enyl n 2 3 4 dimethoxyphenylethyl alpha methylsulfinylacetamide and its derivatives. Journal Of The Chemical Society Perkin Transactions I: 5-610

On being heated with toluene-p-sulfonic acid, N-(cyclohex-1-enyl)-N-[2-(3,4-dimethoxyphenyl)-ethyl]-.alpha.-(methylsulphinyl)acetamide underwent double cyclization to give the erythrinane derivative, which was converted into the amide by reduction with Raney nickel and into the enamide by thermolysis of the corresponding sulfoxide. The double cyclization of the sulfoxide gave a stereoisomeric mixture of the ether products. On treatment with Raney nickel, they afforded a mixture of the alcohols, each of which was oxidized with chromium trioxide-pyridine to give the same ketone. The sulfoxide also cyclized to afford 2 products, but in low yields, which were desulfurized with Raney nickel to give the erythrinones [perhydro-cis-erythrin-11-en-8-one(11,12-didehydroperhydro-cis-erythrinan-8-one) and 14,15,16,17-tetrahydro-cis-erythrinan-8-one].

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