From macrocycle dipeptide lactams to azabicyclo[X.Y.0]alkanone amino acids: a transannular cyclization route for peptide mimic synthesis.
[reaction: see text] Macrocyclic and fused bicyclic dipeptides are complementary motifs for mimicry of different types of beta-turn geometry. Macrocyclic dipeptide mimics have served as precursors for the synthesis of their bicyclic counterparts using electrophilic transannular cyclizations of 9- and 10-membered ring lactams 9-12 to form azabicyclo[4.3.0]- and -[5.3.0]alkanone amino esters 13-16.
Surprenant
Simon
S
Département de Chimie, Université de Montréal, Succursale Centre Ville, Québec, Canada.
Lubell
William D
WD
D000596:Amino Acids / Q000138:chemical synthesis* / Q000737:chemistry; D019086:Bridged Bicyclo Compounds, Heterocyclic / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D003500:Cyclization; D004151:Dipeptides / Q000737:chemistry*; D007769:Lactams / Q000737:chemistry*; D018716:Molecular Mimicry; D015394:Molecular Structure
D000596:Amino Acids; D019086:Bridged Bicyclo Compounds, Heterocyclic; D004151:Dipeptides; D007769:Lactams