title: Total Synthesis of Nominal Cyclocinamide B and Investigation into the Identity of the Cyclocinamides.
abstract: The total synthesis of nominal cyclocinamide B, a cyclic peptide marine natural product, is reported together with an isomer of nominal cyclocinamide A. Initial attempts at the synthesis of the title compounds by inclusion of a turn inducer failed. However, direct synthesis succeeded in formation of the 14-membered cyclic peptide structure. Comparison of the data from all synthetic cyclocinamide A and B compounds with those of the natural products leads to the conclusion that the two natural products possess the same relative stereochemistry and that the true structures have not been defined.
authors.affiliation: Department of Chemistry and Biochemistry, University of California, Santa Cruz, CA 95064.
authors.forename: Stephanie S
authors.initials: SS
authors.lastname: Curzon
authors.affiliation: Department of Chemistry and Biochemistry, University of California, Santa Cruz, CA 95064.
authors.forename: Jessica M
authors.initials: JM
authors.lastname: Garcia
authors.affiliation: Department of Chemistry and Biochemistry, University of California, Santa Cruz, CA 95064.
authors.forename: Joseph P
authors.initials: JP
authors.lastname: Konopelski
keywords: cyclic peptide; natural product synthesis; peptide synthesis; β-amino acids