Applications of multicomponent reactions for the synthesis of diverse heterocyclic scaffolds.
A four-component coupling process involving sequential reactions of aldehydes, primary amines, acid chlorides, and nucleophiles has been developed to prepare multifunctional substrates that may be employed in subsequent ring-forming reactions to generate a diverse array of functionalized heterocyclic scaffolds. This new approach to diversity-oriented synthesis was then applied to the first total synthesis of the isopavine alkaloid (+/-)-roelactamine.
Sunderhaus
James D
JD
Department of Chemistry and Biochemistry, The University of Texas at Austin, Austin Texas 78712, USA.
Dockendorff
Chris
C
Martin
Stephen F
SF
D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D001688:Biological Products / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D003500:Cyclization; D006572:Heterocyclic Compounds, Bridged-Ring / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D028101:Papaveraceae / Q000737:chemistry; D010946:Plants, Medicinal / Q000737:chemistry; D013237:Stereoisomerism
D000470:Alkaloids; D001688:Biological Products; D006572:Heterocyclic Compounds, Bridged-Ring; C524209:roelactamine