title: Enantioselective formal total synthesis of roseophilin.
abstract: [formula: see text] An enantioselective formal total synthesis of roseophilin 3 is presented. The 13-membered ring of macrotricycle 1 was formed via an efficient ring-closing metathesis reaction of bicycle 4. A palladium-catalyzed methoxycarbonylation reaction of enol triflate 5 was utilized to functionalize the right-hand ring of bicycle 2. The allyl substituent was introduced by a radical allylation of alpha-bromoketone 17.
authors.affiliation: Laboratory of Organic Chemistry, University of Amsterdam, The Netherlands.
authors.forename: S J
authors.initials: SJ
authors.lastname: Bamford
authors.forename: T
authors.initials: T
authors.lastname: Luker
authors.forename: W N
authors.initials: WN
authors.lastname: Speckamp
authors.forename: H
authors.initials: H
authors.lastname: Hiemstra
mesh_terms: D006575:Heterocyclic Compounds, 3-Ring / Q000138:chemical synthesis / Q000737:chemistry; D011758:Pyrroles / Q000138:chemical synthesis / Q000737:chemistry; D013237:Stereoisomerism; D013302:Streptomyces / Q000737:chemistry*
chemical_list: D006575:Heterocyclic Compounds, 3-Ring; D011758:Pyrroles; C408872:roseophilin