Pictet-Spengler reactions for the synthesis of pharmaceutically relevant heterocycles.
The synthesis of biologically active heterocyclic scaffolds is one of the significant challenges of modern synthetic chemistry. The Pictet-Spengler (PS) reaction, known for approximately a century, remains a particularly popular cyclization method. This review describes recent applications of the PS reaction in the total synthesis of alkaloids and biologically active analogs of tetrahydroisoquinoline and tetrahydro-β-carboline. The utility of PS cyclization in the synthesis of a range of heterocyclic scaffolds is also described.
University of Warsaw, Faculty of Chemistry, Pasteura 1, 02-093 Warsaw, Poland. karola@chem.uw.edu.pl
Karolina
K
Pulka
D000470:Alkaloids / Q000138:chemical synthesis*; D002243:Carbolines / Q000138:chemical synthesis*; D002626:Chemistry, Pharmaceutical / Q000379:methods*; D003500:Cyclization; D006571:Heterocyclic Compounds / Q000138:chemical synthesis; D015394:Molecular Structure; D013237:Stereoisomerism; D044005:Tetrahydroisoquinolines / Q000138:chemical synthesis*
D000470:Alkaloids; D002243:Carbolines; D006571:Heterocyclic Compounds; D044005:Tetrahydroisoquinolines; C009804:tryptoline