The vinylogous Mannich reaction is rapidly emerging as animportant process for the construction of derivatives of δ-aminocarbonyl compounds. Because the iminium and dienol components employed in this addition may be either acyclic or cyclic, awide variety of adducts may be quickly assembled. These intermediates may then in turn be converted into a broad array ofalkaloids and substituted nitrogen heterocycles. We have developeda number of variations of this reaction and have applied some ofthem to the concise syntheses of a number of structurally diverseand complex alkaloid natural products. Many of these results arepresented in a historical context in this Account.