title: Catalytic asymmetric synthesis of butane diacetal-protected (4S,5S)-dihydroxycyclohexen-1-one and use in natural product synthesis.
abstract: Due to the lack of availability of unnatural (+)-quinic acid as a starting material, a 6-step synthesis of butane diacetal-protected (4S,5S)-dihydroxycyclohexen-1-one (formally derived from (+)-quinic acid) has been devised. The key catalytic asymmetric step involves a chiral Co-salen-catalysed epoxide ring-opening reaction. (4S,5S)-Dihydroxycyclohexen-1-one was utilised in the synthesis of two cyclohexenone natural products isolated from the mycelia of Lasiodiplodia theobromae.
authors.affiliation: Department of Chemistry, University of York, Heslington, York YO10 5DD, UK.
authors.forename: David J
authors.initials: DJ
authors.lastname: Burns
authors.forename: Shuji
authors.initials: S
authors.lastname: Hachisu
authors.forename: Peter
authors.initials: P
authors.lastname: O'Brien
authors.forename: Richard J K
authors.initials: RJ
authors.lastname: Taylor
mesh_terms: D000080:Acetals / Q000737:chemistry*; D001203:Ascomycota / Q000737:chemistry; D001688:Biological Products / Q000138:chemical synthesis* / Q000737:chemistry / Q000302:isolation & purification; D002384:Catalysis; D003035:Cobalt / Q000737:chemistry*; D003512:Cyclohexanones / Q000138:chemical synthesis* / Q000737:chemistry / Q000302:isolation & purification; D005029:Ethylenediamines / Q000737:chemistry*; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000737:chemistry*
chemical_list: C580733:(4S,5S)-dihydroxycyclohexen-1-one; D000080:Acetals; D001688:Biological Products; D003512:Cyclohexanones; D005029:Ethylenediamines; D009942:Organometallic Compounds; D003035:Cobalt; C011452:disalicylaldehyde ethylenediamine