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Acc Chem Res. 2002 Oct;35(10):895-904.

Evolution of the vinylogous Mannich reaction as a key construction for alkaloid synthesis.

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Department of Chemistry and Biochemistry, The University of Texas, Austin, Texas 78712, USA.


The vinylogous Mannich reaction is rapidly emerging as an important process for the construction of derivatives of delta-aminocarbonyl compounds. Because the iminium and dienol components employed in this addition may be either acyclic or cyclic, a wide variety of adducts may be quickly assembled. These intermediates may then in turn be converted into a broad array of alkaloids and substituted nitrogen heterocycles. We have developed a number of variations of this reaction and have applied some of them to the concise syntheses of a number of structurally diverse and complex alkaloid natural products. Many of these results are presented in a historical context in this Account.

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