title: A biogenetically-inspired synthesis of a ring-D model of kinamycin F: insights into the conformation of ring D.
abstract: An efficient three-step construction of the highly oxygenated D-ring of the kinamycin antibiotics is reported for a simple model system. A comparison of the spectroscopic characteristics of the synthetic models with those of natural kinamycin F, which is suspected to be the bioactive form of the kinamycins, leads to the conclusion that the favored D-ring conformation of kinamycin F differs from that of the other partially or fully acylated variants.
authors.affiliation: Department of Chemistry, University of Waterloo, Waterloo, Ontario N2L 3G1, Canada.
authors.forename: Nan
authors.initials: N
authors.lastname: Chen
authors.forename: Marjolaine B
authors.initials: MB
authors.lastname: Carrière
authors.forename: Radoslaw S
authors.initials: RS
authors.lastname: Laufer
authors.forename: Nicholas J
authors.initials: NJ
authors.lastname: Taylor
authors.forename: Gary I
authors.initials: GI
authors.lastname: Dmitrienko
mesh_terms: D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000737:chemistry*; D008958:Models, Molecular; D008968:Molecular Conformation; D015394:Molecular Structure; D011809:Quinones / Q000138:chemical synthesis / Q000737:chemistry; D013302:Streptomyces / Q000737:chemistry; D000095602:Angucyclines and Angucyclinones
chemical_list: D000900:Anti-Bacterial Agents; D011809:Quinones; C059021:kinamycin F; D000095602:Angucyclines and Angucyclinones