title: Total synthesis of (+)-pleuromutilin.
abstract: The first enantiospecific total synthesis of the antibacterial natural product (+)-pleuromutilin has been achieved. The approach includes the synthesis of a non-racemic cyclisation substrate from (+)-trans-dihydrocarvone, a highly selective SmI2-mediated cyclisation cascade, an electron transfer reduction of a hindered ester, and the first efficient conversion of (+)-mutilin to the target.
authors.affiliation: School of Chemistry, The University of Manchester, Oxford Road, Manchester, M13 9PL, UK.
authors.forename: Neal J
authors.initials: NJ
authors.lastname: Fazakerley
authors.forename: Matthew D
authors.initials: MD
authors.lastname: Helm
authors.forename: David J
authors.initials: DJ
authors.lastname: Procter
mesh_terms: D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000737:chemistry; D001688:Biological Products / Q000138:chemical synthesis* / Q000737:chemistry; D003500:Cyclization; D000081005:Cyclohexane Monoterpenes; D004224:Diterpenes / Q000138:chemical synthesis / Q000737:chemistry; D007659:Ketones / Q000737:chemistry*; D015394:Molecular Structure; D039821:Monoterpenes / Q000138:chemical synthesis / Q000737:chemistry; D011083:Polycyclic Compounds / Q000737:chemistry*; D013237:Stereoisomerism; D000097567:Pleuromutilins
chemical_list: D000900:Anti-Bacterial Agents; D001688:Biological Products; D000081005:Cyclohexane Monoterpenes; D004224:Diterpenes; D007659:Ketones; D039821:Monoterpenes; D011083:Polycyclic Compounds; D000097567:Pleuromutilins; C475718:mutilin; C556859:dihydrocarvone