The Pictet-Spengler reaction in solid-phase combinatorial chemistry.
The Pictet-Spengler reaction is an important reaction for the generation of tetrahydro-beta-carbolines and tetrahydroisoquinoline ring systems, which exhibit a range of biological and pharmacological properties. This review covers the solid-phase Pictet-Spengler reaction, as employed in solid-phase routes toward a range of complex heterocyclic ring systems, with focus on experimental conditions, efficiency and diastereoselectivity. This is illustrated by the application of this reaction to the synthesis of combinatorial libraries, natural product analogs and drug-like scaffolds.
Nielsen
Thomas E
TE
Carlsberg Laboratory, Department of Chemistry, Gamle Carlsberg Vej 10, DK-2500 Valby, Denmark. mpm@crc.dk
Diness
Frederik
F
Meldal
Morten
M
D002243:Carbolines / Q000138:chemical synthesis; D002626:Chemistry, Pharmaceutical; D020650:Combinatorial Chemistry Techniques / Q000379:methods*; D003718:Denmark; D006571:Heterocyclic Compounds / Q000138:chemical synthesis; D015394:Molecular Structure; D044005:Tetrahydroisoquinolines / Q000138:chemical synthesis
D002243:Carbolines; D006571:Heterocyclic Compounds; D044005:Tetrahydroisoquinolines