title: Total synthesis of nominal (11S)- and (11R)-cyclocinamide A.
abstract: The cyclocinamides possess a unique β(2)αβ(2)α 14-membered tetrapeptide core. The initially reported biological data and intriguing structure, which was without full stereochemical identification, necessitated synthesis of both nominal (all-S) cyclocinamide A and the 11R isomer. The completed synthesis is highlighted by the use of a (cyclo)asparagine-containing dipeptide as a turn inducing fragment. Due to inconsistencies in analytical data between natural and synthetic samples, a re-evaluation of the natural product stereochemistry appears necessary.
authors.affiliation: Department of Chemistry and Biochemistry, University of California, Santa Cruz, California 95064, USA.
authors.forename: Jessica M
authors.initials: JM
authors.lastname: Garcia
authors.forename: Stephanie S
authors.initials: SS
authors.lastname: Curzon
authors.forename: Katharine R
authors.initials: KR
authors.lastname: Watts
authors.forename: Joseph P
authors.initials: JP
authors.lastname: Konopelski
mesh_terms: D001688:Biological Products / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D010456:Peptides, Cyclic / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D001688:Biological Products; D010456:Peptides, Cyclic; C533363:cyclocinamide A