Sequential five-component synthesis of spiropyrrolidinochromanones.
Herein we report a novel, diastereoselective, one-pot, two-step, sequential synthesis of highly functionalized natural product-like spiropyrrolidinochromanones. The process consists of an Ugi four-component condensation of 3-formylchromones with amines, isocyanides, and glyoxylic acids followed by a nucleophilic conjugate addition and intramolecular cyclization. The experimental simplicity and tolerance to a wide variety of substituents makes this method suitable for combinatorial synthesis.
Marcaccini
Stefano
S
Dipartimento di Chimica Organica Ugo Schiff, Università di Firenze, 50019 Sesto Fiorentino FI, Italy. stefano.marcaccini@unifi.it
Neo
Ana G
AG
Marcos
Carlos F
CF
D000588:Amines / Q000737:chemistry; D002244:Carbon / Q000737:chemistry; D002625:Chemistry, Organic / Q000379:methods; D002626:Chemistry, Pharmaceutical / Q000379:methods*; D002839:Chromans / Q000138:chemical synthesis* / Q000737:chemistry; D003486:Cyanides / Q000737:chemistry; D003500:Cyclization; D015195:Drug Design; D006038:Glyoxylates / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D008956:Models, Chemical; D008968:Molecular Conformation; D012997:Solvents / Q000737:chemistry; D013141:Spiro Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D000588:Amines; D002839:Chromans; D003486:Cyanides; D006038:Glyoxylates; D012997:Solvents; D013141:Spiro Compounds; D002244:Carbon; C031150:glyoxylic acid