Synthesis and solid state conformation of phenylalanine mimetics constrained in a proline-like conformation.
We present the synthesis of five- and six-membered cyclic phenylalanine mimics (1, 9, 16 and 17) that are constrained in a proline-like conformation. The five-membered mimetic 16 was prepared by Ring Closing Metathesis (RCM) of diene 15, itself prepared by alpha-benzylation of the L-methionine derived oxazolidinone 10, followed by oxidative elimination, ring hydrolysis and N-allylation. The six-membered mimetic 1 was prepared by allylating the L-phenylalanine-derived oxazolidinone 5, followed by hydrolysis, N-allylation and RCM. Olefins 1 and 16 were catalytically hydrogenated to give 9 and 17, respectively. The solid state structures of 9 and 16 were determined by X-ray crystallography and their conformations compared with that of 1.
Gardiner
James
J
Department of Chemistry, University of Canterbury, Christchurch, New Zealand.
Abell
Andrew D
AD
D040761:Biomimetic Materials / Q000138:chemical synthesis* / Q000737:chemistry*; D002384:Catalysis; D018360:Crystallography, X-Ray; D008968:Molecular Conformation; D010649:Phenylalanine / Q000737:chemistry*; D011392:Proline / Q000737:chemistry*
D010649:Phenylalanine; D011392:Proline