title: A furan Diels-Alder cycloaddition approach to scyphostatin analogues.
abstract: The synthesis of two diastereoisomers of the epoxycyclohexenone core of scyphostatin, a naturally occurring sphingomyelinase inhibitor, has been achieved via a common oxabicyclic intermediate. The diastereomeric intermediates are accessed by stereodivergent oxidative functionalisation processes, followed by a Lewis acid mediated ring opening rearrangement reaction.
authors.affiliation: Department of Chemistry, University of Sheffield, Sheffield, S3 7HF, UK.
authors.forename: Calum J
authors.initials: CJ
authors.lastname: Fraser
authors.forename: Gareth P
authors.initials: GP
authors.lastname: Howell
authors.forename: Joseph P A
authors.initials: JP
authors.lastname: Harrity
mesh_terms: D000577:Amides / Q000138:chemical synthesis* / Q000737:chemistry*; D061565:Cycloaddition Reaction; D004852:Epoxy Compounds / Q000737:chemistry; D005663:Furans / Q000737:chemistry*; D011753:Pyrones / Q000138:chemical synthesis* / Q000737:chemistry*
chemical_list: D000577:Amides; D004852:Epoxy Compounds; D005663:Furans; D011753:Pyrones; C121123:scyphostatin; C039281:furan