A formal total synthesis of roseophilin: cyclopentannelation approach to the macrocyclic core.
[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.
Harrington
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PE
Department of Chemistry, University of Hawaii at Manoa, Honolulu 96822, USA.
Tius
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MA
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
D003517:Cyclopentanes; D006575:Heterocyclic Compounds, 3-Ring; D011758:Pyrroles; C408872:roseophilin