title: A stereoselective, Sm(II)-mediated approach to decorated cis-hydrindanes: synthetic studies on faurinone and pleuromutilin.
abstract: The cis-hydrindane motif is found in a number of natural products that display important biological activity. A flexible, stereoselective approach to the framework has been developed that features highly diastereoselective, SmI(2)-mediated cyclisations. The strategy has been exploited in the first synthesis of the proposed structure of faurinone and an approach to the skeleton of the antibacterial natural product, pleuromutilin.
authors.affiliation: School of Chemistry, The University of Manchester, Oxford Road, Manchester, M13 9PL, UK.
authors.forename: Thomas J K
authors.initials: TJ
authors.lastname: Findley
authors.forename: David
authors.initials: D
authors.lastname: Sucunza
authors.forename: Laura C
authors.initials: LC
authors.lastname: Miller
authors.forename: Matthew D
authors.initials: MD
authors.lastname: Helm
authors.forename: Madeleine
authors.initials: M
authors.lastname: Helliwell
authors.forename: David T
authors.initials: DT
authors.lastname: Davies
authors.forename: David J
authors.initials: DJ
authors.lastname: Procter
mesh_terms: D001688:Biological Products / Q000737:chemistry; D003500:Cyclization; D004224:Diterpenes / Q000138:chemical synthesis; D006576:Heterocyclic Compounds, 4 or More Rings / Q000138:chemical synthesis*; D007189:Indans / Q000737:chemistry*; D008958:Models, Molecular; D015394:Molecular Structure; D010084:Oxidation-Reduction; D011083:Polycyclic Compounds; D012493:Samarium / Q000737:chemistry*; D013237:Stereoisomerism; D000097567:Pleuromutilins
chemical_list: D001688:Biological Products; D004224:Diterpenes; D006576:Heterocyclic Compounds, 4 or More Rings; D007189:Indans; D011083:Polycyclic Compounds; D012493:Samarium; D000097567:Pleuromutilins; C531996:faurinone; C531997:hydrindane