Modular synthesis of tetrahydrofluorenones from 5-alkylidene Meldrum's acids.
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.
Fillion
Eric
E
Department of Chemistry, University of Waterloo, Waterloo, Ontario N2L 3G1, Canada. efillion@uwaterloo.ca
Dumas
Aaron M
AM
Hogg
Sylvia A
SA
D000475:Alkenes / Q000737:chemistry*; D004146:Dioxanes / Q000737:chemistry*; D005449:Fluorenes / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism
D000475:Alkenes; D004146:Dioxanes; D005449:Fluorenes; C076489:Meldrum's acid