title: Enantioselective synthesis of the predominant AB ring system of the Schisandra nortriterpenoid natural products.
abstract: An enantioselective synthesis of the AB ring system common to the majority of the Schisandra nortriterpenoid natural products is reported. Key steps include a stereospecific ring opening of a trisubstituted epoxide and the use of a β-lactone to enable installation of the gem-dimethyl functionality of the B ring. An acetalization strategy played a key role in a late-stage biomimetic AB ring bicyclization.
authors.affiliation: Chemistry Research Laboratory, University of Oxford , 12 Mansfield Road, Oxford, OX1 3TA, U.K.
authors.forename: Birgit
authors.initials: B
authors.lastname: Gockel
authors.forename: Shermin S
authors.initials: SS
authors.lastname: Goh
authors.forename: Emma J
authors.initials: EJ
authors.lastname: Puttock
authors.forename: Hannah
authors.initials: H
authors.lastname: Baars
authors.forename: Guilhem
authors.initials: G
authors.lastname: Chaubet
authors.forename: Edward A
authors.initials: EA
authors.lastname: Anderson
mesh_terms: D001688:Biological Products / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D003500:Cyclization; D007783:Lactones / Q000737:chemistry; D015394:Molecular Structure; D032141:Schisandra / Q000737:chemistry*; D013237:Stereoisomerism; D014315:Triterpenes / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D001688:Biological Products; D007783:Lactones; D014315:Triterpenes