title: Total synthesis of (+)-cis-sylvaticin: double oxidative cyclization reactions catalyzed by osmium.
abstract: The double oxidative cyclization of dienes is a viable procedure for making complex natural products containing cis-THF units. A double deprotection/double oxidative cyclization strategy using catalytic osmium tetroxide was used to construct the bisheterocyclic core of cis-sylvaticin and ultimately confirm its structure. The natural product was then prepared by a short sequence of reactions that is exceptionally concise: the final route being just 13 linear steps and 19 chemical operations in total.
authors.affiliation: Department of Chemistry, University of Oxford, Chemistry Research Laboratory, UK. timothy.donohoe@chem.ox.ac.uk
authors.forename: Timothy J
authors.initials: TJ
authors.lastname: Donohoe
authors.forename: Robert M
authors.initials: RM
authors.lastname: Harris
authors.forename: Jeremy
authors.initials: J
authors.lastname: Burrows
authors.forename: Jeremy
authors.initials: J
authors.lastname: Parker
mesh_terms: D002384:Catalysis; D003500:Cyclization; D005663:Furans / Q000138:chemical synthesis*; D009682:Magnetic Resonance Spectroscopy; D008956:Models, Chemical; D009992:Osmium / Q000737:chemistry*; D010084:Oxidation-Reduction; D018515:Plant Leaves / Q000737:chemistry*; D010946:Plants, Medicinal / Q000737:chemistry*; D031045:Rollinia / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D005663:Furans; C063434:sylvaticin; D009992:Osmium