Evolution of the Vinylogous Mannich Reaction as a Key Construction for Alkaloid Synthesis
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- 19 June 2002
- journal article
- review article
- Published by American Chemical Society (ACS) in Accounts of Chemical Research
- Vol. 35 (10) , 895-904
- https://doi.org/10.1021/ar950230w
Abstract
The vinylogous Mannich reaction is rapidly emerging as an important 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, 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.Keywords
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