title: Diastereoselective Synthesis and Conformational Analysis of (2R)- and (2S)-Fluorostatines: An Approach Based on Organocatalytic Fluorination of a Chiral Aldehyde.
abstract: Stereoselectively fluorinated analogues of the amino acid statine have been efficiently synthesized. The key step is an organocatalytic electrophilic fluorination of a chiral β-oxygenated aldehyde, which provided a test of both diastereoselectivity and chemoselectivity. The target statine analogues were found to adopt unique conformations influenced by the fluorine gauche effect, rendering them potentially valuable building blocks for incorporation into bioactive peptides.
authors: National Engineering Research Center for Carbohydrate Synthesis, Jiangxi Normal University , Nanchang 330022, China.|School of Chemistry, UNSW Australia , Sydney, NSW 2052, Australia.
authors: Xiang-Guo
authors: XG
authors: Hu
authors: School of Chemistry, UNSW Australia , Sydney, NSW 2052, Australia.
authors: Aggie
authors: A
authors: Lawer
authors: School of Chemistry, UNSW Australia , Sydney, NSW 2052, Australia.|Department of Chemistry and Biomolecular Sciences, Macquarie University , Sydney, NSW 2109, Australia.
authors: Matthew B
authors: MB
authors: Peterson
authors: School of Chemistry, UNSW Australia , Sydney, NSW 2052, Australia.
authors: Hasti
authors: H
authors: Iranmanesh
authors: School of Chemistry, UNSW Australia , Sydney, NSW 2052, Australia.
authors: Graham E
authors: GE
authors: Ball
authors: School of Chemistry, UNSW Australia , Sydney, NSW 2052, Australia.
authors: Luke
authors: L
authors: Hunter
mesh_terms: D000447:Aldehydes / Q000737:chemistry; D000596:Amino Acids / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D005461:Fluorine / Q000737:chemistry; D054879:Halogenation; D006845:Hydrocarbons, Fluorinated / Q000138:chemical synthesis* / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D008968:Molecular Conformation; D015394:Molecular Structure; D010436:Pepstatins / Q000737:chemistry / Q000494:pharmacology; D013237:Stereoisomerism
chemical_list: D000447:Aldehydes; D000596:Amino Acids; D006845:Hydrocarbons, Fluorinated; D010436:Pepstatins; D005461:Fluorine; C031375:pepstatin; C013165:statine