title: Modular synthesis of tetrahydrofluorenones from 5-alkylidene Meldrum's acids.
abstract: The one-pot synthesis of tetrahydrofluorenones, the core 6-5-6 tricyclic structural motif found in norditerpenoid natural products, from alkylidene Meldrum's acids via thermal Diels-Alder/BF3.OEt2-catalyzed Friedel-Crafts acylation reactions is described. A series of tetrahydrofluorenones was assembled in good yields, and the Diels-Alder/Friedel-Crafts acylation protocol allowed modification of the substitution within the rings.
authors.affiliation: Department of Chemistry, University of Waterloo, Waterloo, Ontario N2L 3G1, Canada. efillion@uwaterloo.ca
authors.forename: Eric
authors.initials: E
authors.lastname: Fillion
authors.forename: Aaron M
authors.initials: AM
authors.lastname: Dumas
authors.forename: Sylvia A
authors.initials: SA
authors.lastname: Hogg
mesh_terms: D000475:Alkenes / Q000737:chemistry*; D004146:Dioxanes / Q000737:chemistry*; D005449:Fluorenes / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D000475:Alkenes; D004146:Dioxanes; D005449:Fluorenes; C076489:Meldrum's acid