title: Enantioselective synthesis of putative lipiarmycin aglycon related to fidaxomicin/tiacumicin B.
abstract: An enantioselective synthesis of a putative lipiarmycin aglycon was accomplished and features: 1) Brown's enantioselective alkoxyallylboration and allylation of aldehydes, 2) chain elongation by iterative Horner-Wadsworth-Emmons olefination, 3) Evans' aldol reaction and 4) an ene-diene ring-closing metathesis. A neighboring-group-assisted chemoselective reductive desilylation was uncovered in this study and was instrumental to the realization of the present synthesis.
authors.affiliation: Centre de Recherche de Gif, Laboratoire International Associé, Institut de Chimie des Substances Naturelles, CNRS, 91198 Gif-sur-Yvette Cedex (France).
authors.forename: William
authors.initials: W
authors.lastname: Erb
authors.forename: Jean-Marie
authors.initials: JM
authors.lastname: Grassot
authors.forename: David
authors.initials: D
authors.lastname: Linder
authors.forename: Luc
authors.initials: L
authors.lastname: Neuville
authors.forename: Jieping
authors.initials: J
authors.lastname: Zhu
mesh_terms: D000617:Aminoglycosides / Q000138:chemical synthesis* / Q000737:chemistry; D000077732:Fidaxomicin; D013237:Stereoisomerism
chemical_list: D000617:Aminoglycosides; D000077732:Fidaxomicin
keywords: macrocycles; metathesis; natural products; protecting groups; total synthesis