Solid-phase synthesis of thalidomide and its analogues.
A novel solid-phase synthesis of thalidomide and its metabolites and analogues is described. The synthetic strategy involves the coupling of hydroxymethyl polystyrene with phthalic anhydride to form the resin-linked acid. The acid is then reacted with primary amines followed by acid or base treatment to form thalidomide and its analogues with either open or closed phthalimide rings. Most of the analogues are synthesized with high yields (40.3-98.1% in three steps) and purities (92.3-98.9%).
Xiao
Zili
Z
Division of Medicinal Chemistry and Pharmacognosy, College of Pharmacy, The Ohio State University, 500 West 12th Avenue, Columbus, Ohio 43210, USA.
Schaefer
Kevin
K
Firestine
Steven
S
Li
Pui-Kai
PK
D020533:Angiogenesis Inhibitors / Q000138:chemical synthesis*; D020650:Combinatorial Chemistry Techniques; D006801:Humans; D013792:Thalidomide / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000494:pharmacology
D020533:Angiogenesis Inhibitors; D013792:Thalidomide