title: Stereoselective bromination-suzuki cross-coupling of dehydroamino acids to form novel reverse-turn peptidomimetics: substituted unsaturated and saturated indolizidinone amino acids.
abstract: A general and efficient methodology has been developed to prepare the C4-substituted dipeptide reverse-turn mimetics unsaturated (9a, 10a) and saturated (11a) azabicyclo[4.3.0] alkane amino acid derivatives. The side chain was introduced by bromination of dehydroamino acid intermediates followed by Suzuki coupling. Hydrogenation of the bicyclic dehydroamino acid 9a afforded saturated bicyclic lactam 11a. This approach can be further explored for the synthesis of a variety of such beta-turn mimetics with aryl and alkyl side chain functionalities. [reaction: see text]
authors.affiliation: Department of Chemistry, University of Arizona, Tucson, AZ 85721, USA.
authors.forename: Junyi
authors.initials: J
authors.lastname: Zhang
authors.forename: Chiyi
authors.initials: C
authors.lastname: Xiong
authors.forename: Wei
authors.initials: W
authors.lastname: Wang
authors.forename: Jinfa
authors.initials: J
authors.lastname: Ying
authors.forename: Victor J
authors.initials: VJ
authors.lastname: Hruby
mesh_terms: D000596:Amino Acids / Q000737:chemistry*; D007202:Indicators and Reagents; D007212:Indolizines / Q000737:chemistry*; D010455:Peptides / Q000138:chemical synthesis*; D013237:Stereoisomerism
chemical_list: D000596:Amino Acids; D007202:Indicators and Reagents; D007212:Indolizines; D010455:Peptides