title: A formal total synthesis of roseophilin: cyclopentannelation approach to the macrocyclic core.
abstract: [formula: see text] The formal total synthesis of the macrocyclic core of roseophilin 4 has been accomplished in 12 steps from 5-hexenal 8. The cyclopentannelation reaction was used to form the aliphatic five-membered ring of 3. Diene 2 was assembled by means of a Stetter reaction. Ring-closing metathesis of 2, reduction, and Knorr reaction of the 1,4-diketone 5 gave the ketopyrrole 3.
authors.affiliation: Department of Chemistry, University of Hawaii at Manoa, Honolulu 96822, USA.
authors.forename: P E
authors.initials: PE
authors.lastname: Harrington
authors.forename: M A
authors.initials: MA
authors.lastname: Tius
mesh_terms: D003517:Cyclopentanes / Q000737:chemistry; D006575:Heterocyclic Compounds, 3-Ring / Q000138:chemical synthesis / Q000737:chemistry; D010084:Oxidation-Reduction; D011758:Pyrroles / Q000138:chemical synthesis / Q000737:chemistry; D013302:Streptomyces / Q000737:chemistry
chemical_list: D003517:Cyclopentanes; D006575:Heterocyclic Compounds, 3-Ring; D011758:Pyrroles; C408872:roseophilin