title: Resolution of an iridoid synthon, gastrolactol, by means of dynamic acetylation and lipase-catalyzed alcoholysis.
abstract: A short synthetic route to asymmetric iridoids was developed. The three key steps were an intramolecular [4 + 2] cycloaddition reaction of an enamine derivative of 8-oxocitral (2), a dynamic acetylation, and an enzymatic resolution of the gastrolactyl acetates 5a and 5b, iridoids with three stereocenters. Some regio- and stereoselective heterogeneous catalytic hydrogenations of double bonds in iridoid aglucones were discussed.
authors.affiliation: Department of Organic Chemistry, Royal Institute of Technology, SE -100 44 Stockholm, Sweden.
authors.forename: E M
authors.initials: EM
authors.lastname: Santangelo
authors.forename: D
authors.initials: D
authors.lastname: Rotticci
authors.forename: I
authors.initials: I
authors.lastname: Liblikas
authors.forename: T
authors.initials: T
authors.lastname: Norin
authors.forename: C R
authors.initials: CR
authors.lastname: Unelius
mesh_terms: D000107:Acetylation; D002384:Catalysis; D008049:Lipase / Q000378:metabolism*; D008968:Molecular Conformation; D013729:Terpenes / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D013729:Terpenes; C434291:gastrolactol; D008049:Lipase