title: Nonenzymic polycyclization of analogues of oxidosqualene with a preformed C-ring.
abstract: Some nonenzymic epoxide-initiated polyolefin cyclization are reported. The presented molecules are partially constrained analogues of (3S)-oxidosqualene, the natural substrate to many important cyclase enzymes. These model compounds feature a preformed C-ring with built-in stereochemical information. The experimental results allow for an instructive comparison with the enzymic processes, particularly those of the cyclases in steroid biosynthesis (i.e. lanosterol synthase).
authors.affiliation: Ghent University, Department of Organic Chemistry, Krijgslaan 281 (S4), B-9000 Gent, Belgium.
authors.forename: Johan M
authors.initials: JM
authors.lastname: Winne
authors.forename: Pierre J
authors.initials: PJ
authors.lastname: De Clercq
authors.forename: Marco
authors.initials: M
authors.lastname: Milanesio
authors.forename: Philip
authors.initials: P
authors.lastname: Pattison
authors.forename: Davide
authors.initials: D
authors.lastname: Viterbo
mesh_terms: D003500:Cyclization; D008958:Models, Molecular; D008968:Molecular Conformation; D013185:Squalene / Q000031:analogs & derivatives* / Q000737:chemistry
chemical_list: C520393:oxidosqualene; D013185:Squalene