title: Synthesis and structure of preorganized, C(3)-symmetric trilactam scaffolds with convergently oriented (S)-acetylthiomethyl appendages.
abstract: [reaction: see text] Efficient modular synthesis of conformationally preorganized, C(3)-symmetric trilactams is reported. The allyl acetate cyclization substrate was synthesized in five steps from Garner's L-serine-derived aldehyde. After chiral ligand-mediated palladium cyclization, the resulting vinyl hydropyran was transformed into the orthogonally protected amino acids for iterative coupling. The final macrolactamization was accomplished using EDCI/HOBt or HATU/HOAt under high dilution conditions.
authors.affiliation: Department of Chemistry, University of Wisconsin-Madison, 1101 University Avenue, Madison, Wisconsin 53706-1396, USA.
authors.forename: John E
authors.initials: JE
authors.lastname: Campbell
authors.forename: Erikah E
authors.initials: EE
authors.lastname: Englund
authors.forename: Steven D
authors.initials: SD
authors.lastname: Burke
mesh_terms: D002384:Catalysis; D018360:Crystallography, X-Ray; D003500:Cyclization; D006575:Heterocyclic Compounds, 3-Ring / Q000138:chemical synthesis* / Q000737:chemistry; D007769:Lactams / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism; D013438:Sulfhydryl Compounds / Q000737:chemistry
chemical_list: D006575:Heterocyclic Compounds, 3-Ring; D007769:Lactams; D013438:Sulfhydryl Compounds