Efficient formal total synthesis of the erythrina alkaloid (+)-erysotramidine, using a domino process.
A domino process consisting of an amidation, spirocyclization, and formation of an iminium ion and electrophilic aromatic substitution of a phenylethylamine and a ketoester leads to the spirocyclic skeleton of (+)-erysotramidine, which can be further transformed into the natural alkaloid.
Tietze
Lutz F
LF
Institute of Organic and Biomolecular Chemistry, Georg-August University Göttingen, Germany. ltietze@gwdg.de
Tölle
Nina
N
Kratzert
Daniel
D
Stalke
Dietmar
D
D000577:Amides / Q000737:chemistry; D018360:Crystallography, X-Ray; D003500:Cyclization; D006576:Heterocyclic Compounds, 4 or More Rings / Q000138:chemical synthesis* / Q000737:chemistry; D008958:Models, Molecular; D015394:Molecular Structure; D013237:Stereoisomerism
D000577:Amides; D006576:Heterocyclic Compounds, 4 or More Rings; C492626:erysotramidine