Evolution of the vinylogous Mannich reaction as a key construction for alkaloid synthesis.
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.
Martin
Stephen F
SF
Department of Chemistry and Biochemistry, The University of Texas, Austin, Texas 78712, USA.
D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D002625:Chemistry, Organic; D005663:Furans / Q000737:chemistry; D015394:Molecular Structure; D055601:Organic Chemistry Phenomena
D000470:Alkaloids; D005663:Furans