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The first observation of ring cleavage between positions 1 and 2 of a 1,4-dihydropyrimidine skeleton was reported upon the nucleophilic addition of 4,6-unsubstituted 1,4-dihydropyrimidine with 3equiv of an aniline derivative or phenylhydrazine in the presence of 0.1equiv of pyridinium p-toluenesulfonate (PPTS) in CH 2 Cl 2 ; the nucleophilic reactions of 4-methyl-6-unsubstituted 1,6(3,4)-dihydropyrimidine...
Stereocontrolled biomimetic total syntheses of the title compounds are described. Our syntheses feature a highly efficient preparation of the key intermediate 11 using our novel indole synthesis methodology. A novel amine protecting protocol by means of 2,4-dinitrobenzenesulfonamides has been developed to ensure the formation of the elusive secodine (3) as well as secodine-type intermediate (4)...
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