title: Studies on the synthesis of valienamine and 1-epi-valienamine starting from D-glucose or L-sorbose.
abstract: Two synthetic routes to a carbocyclic precursor to valienamine are reported, starting from either D-glucose or L-sorbose and using ring-closing metathesis as a key step. A low-yielding synthesis of 1-epi-valienamine is reported. Results from an abortive third possible route to valienamine based on an early introduction of nitrogen are discussed.
authors.affiliation: Department of Organic Chemistry, The Arrhenius Laboratory, Stockholm University, 106 91 Stockholm, Sweden.
authors.forename: Ian
authors.initials: I
authors.lastname: Cumpstey
authors.forename: Sebastian
authors.initials: S
authors.lastname: Gehrke
authors.forename: Sayeh
authors.initials: S
authors.lastname: Erfan
authors.forename: Riccardo
authors.initials: R
authors.lastname: Cribiu
mesh_terms: D053138:Cyclohexenes / Q000138:chemical synthesis*; D005947:Glucose / Q000737:chemistry*; D006595:Hexosamines / Q000138:chemical synthesis*; D013013:Sorbose / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D053138:Cyclohexenes; D006595:Hexosamines; C030791:valienamine; D005947:Glucose; D013013:Sorbose