title: An asymmetric synthesis of L-pyrrolysine.
abstract: An efficient asymmetric synthesis of the 22nd amino acid L-pyrrolysine has been accomplished. The key stereogenic centers were installed by an asymmetric conjugate addition reaction. A Staudinger/aza-Wittig cyclization was used to form the acid-sensitive pyrroline ring. Pyrrolysine was synthesized in 13 steps in 20% overall yield.
authors.affiliation: Department of Chemistry, University of Wisconsin-Madison, Madison, Wisconsin 53706, United States.
authors.forename: Margaret L
authors.initials: ML
authors.lastname: Wong
authors.forename: Ilia A
authors.initials: IA
authors.lastname: Guzei
authors.forename: Laura L
authors.initials: LL
authors.lastname: Kiessling
mesh_terms: D018360:Crystallography, X-Ray; D003500:Cyclization; D008239:Lysine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D008968:Molecular Conformation; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: C456839:pyrrolysine; D008239:Lysine