Synthesis and chiroptical properties of 5, 7-dioxobicyclo [2.2. 2] oct-2-ene and bicyclo [2.2. 2] octane-2, 5-dione

…, JR Peterson, JA Walsh, LA Paquette

Index: Hill, Richard K.; Morton, Gerald H.; Peterson, John R.; Walsh, James A.; Paquette, Leo A. Journal of Organic Chemistry, 1985 , vol. 50, # 26 p. 5528 - 5533

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Citation Number: 30

Abstract

5, 7-Dioxobicyclo [2.2. 2] oct-2-ene (5) and its dihydro derivative 9 were obtained in racemic form by sequential Diels-Alder addition of maleic anhydride to hydroquinone, hydrolysis of the adduct to diacid 7, oxidative decarboxylation of 7 with lead tetraacetate, and catalytic hydrogenation. Partial resolution of 7 with brucine or quinine afforded (-)-5 in 8046% enantiomeric purity. Ketalization of (f)-5 with diethyl (R, R)-(+)-tartrate and subsequent ...