title: A scalable synthesis of 2S-hydroxymutilin via a modified Rubottom oxidation.
abstract: A scalable synthesis of 2S-hydroxymutilin from pleuromutilin was developed. The synthesis is highlighted by the Rubottom oxidation of a silyl enol ether, conducted in the presence of acetic acid and pyridine, which allows for an efficient and selective oxidation.
authors.affiliation: Chemical Development, GlaxoSmithKline, 709 Swedeland Road, King of Prussia, Pennsylvania 19406, USA. huan.2.wang@gsk.com
authors.forename: Huan
authors.initials: H
authors.lastname: Wang
authors.forename: Yemane W
authors.initials: YW
authors.lastname: Andemichael
authors.forename: Frederick G
authors.initials: FG
authors.lastname: Vogt
mesh_terms: D004224:Diterpenes / Q000737:chemistry; D007659:Ketones / Q000138:chemical synthesis* / Q000737:chemistry; D008968:Molecular Conformation; D010084:Oxidation-Reduction; D011083:Polycyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D000097567:Pleuromutilins
chemical_list: D004224:Diterpenes; D007659:Ketones; D011083:Polycyclic Compounds; D000097567:Pleuromutilins; C534902:2S-hydroxymutilin