title: Antineoplastic agents. 561. Total synthesis of respirantin.
abstract: Total synthesis of the 18-membered ring cyclodepsipeptide believed to be respirantin (1b) has been achieved. The key step in the synthesis is an intramolecular transesterification of the beta-ketoester alcohol 6 to afford the protected macrocycle 5. The synthetic product was shown to be identical to a natural product presumed to be respirantin (1b), and the absolute stereochemistry of six of the seven asymmetric centers of cyclodepsipeptide 1b was unequivocally established. Respirantin (1b) was found to be a remarkable inhibitor of cancer cell growth and related to the antimycin family of antibiotics.
authors.affiliation: Cancer Research Institute and Department of Chemistry and Biochemistry, Arizona State University, PO Box 872404, Tempe, Arizona 85287-2404, USA. bpettit@asu.edu
authors.forename: George R
authors.initials: GR
authors.lastname: Pettit
authors.forename: Thomas H
authors.initials: TH
authors.lastname: Smith
authors.forename: Song
authors.initials: S
authors.lastname: Feng
authors.forename: John C
authors.initials: JC
authors.lastname: Knight
authors.forename: Rui
authors.initials: R
authors.lastname: Tan
authors.forename: Robin K
authors.initials: RK
authors.lastname: Pettit
authors.forename: Peter A
authors.initials: PA
authors.lastname: Hinrichs
mesh_terms: D000818:Animals; D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D003455:Cryptococcus neoformans / Q000187:drug effects; D047630:Depsipeptides / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D004354:Drug Screening Assays, Antitumor; D006801:Humans; D051379:Mice; D008826:Microbial Sensitivity Tests; D015394:Molecular Structure; D013329:Structure-Activity Relationship
chemical_list: D000970:Antineoplastic Agents; D047630:Depsipeptides; C081425:respirantin