Dissolving metal conjugate reduction synthesis

Acrylonitrile (2) has also been used for heterocycle formation from p-diketone substrates. Conjugate addition of 185 to acrylonitrile produced 186 with previously reported conditions,2 and cyclization under hydrolytic conditions generated the corresponding lactam 187 (Scheme 15).65 Dissolving metal reduction provided the trans ring fused product 188, which was subsequently converted to 189. Reduction of 189 completed the synthesis of the Lycopodium alkaloid ( )-Na-methyl-A p-acetylphlegmarine (190) as a mixture of 4 diastereomers. 

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