A scalable synthesis of 2S-hydroxymutilin via a modified Rubottom oxidation.
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.
Wang
Huan
H
Chemical Development, GlaxoSmithKline, 709 Swedeland Road, King of Prussia, Pennsylvania 19406, USA. huan.2.wang@gsk.com
Andemichael
Yemane W
YW
Vogt
Frederick G
FG
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
D004224:Diterpenes; D007659:Ketones; D011083:Polycyclic Compounds; D000097567:Pleuromutilins; C534902:2S-hydroxymutilin