Synthesis of conduritol a from benzoquinone using 9-benzyloxymethoxyanthracene as a protecting and directing group

Improved synthesis of 5-(t-butyldimethylsilyloxymethyl)-2-methyl-5,6-dihydrocyclopenta[c]pyrrole-1,3(2H,4H)-dione from N-methylmaleimide

“…5 Thus, the above result was not fully unexpected. Knapp et al 6 had shown that the Diels-Alder adducts derived from 9-(benzyloxymethoxy)anthracene can easily experience the retro-Diels-Alder reaction by hydrolysis of the benzyloxymethoxy group and treatment of the resulting alcohol with potassium hydride in anhydrous 1,4-dioxane or THF at 25 ºC. Other authors have also carried out similar retro-Diels-Alder reactions.…”

Structure of cis-9-[(benzyloxy)methoxy]-4a,9,9a,10-tetrahydro-9,10-o-benzenoanthracene-1,4-dione, a sterically congested 2-ene-1,4-dione

“…Title compound prepared by Diels-Alder reaction of 9-[(benzyloxy)methoxy]anthracene with p-benzoquinone (Knapp et al, 1983 Main, Hull, Lessinger, Germain, Declercq & Woolfson, 1978); E map based on 300 phases revealed all 32 non-H atoms. H atoms at calculated positions with C--H distance = 0.95 A.…”

“…As part of our work on aminocyclitol synthesis (Knapp, Ornaf & Rodriques, 1983), we became interested in site-selective reduction reactions of the 2-ene-1,4-dione (1). Specifically, reaction conditions were sought under which the C(4) carbonyl group * To whom correspondence should be addressed.…”

Lewis Acid-Catalyzed Reactions of Anthrone: Preference for Cycloaddition Reaction over Conjugate Addition Depending on the Functionality of α,β-Unsaturated Carbonyl Compounds

“…Reported attempts have involved the treatment of anthrone with a highly reactive dienophile, such as dimethyl acetylenedicarboxylate or maleic anhydride in boiling acetic acid. 6 On the other hand, anthracenolate ion also acts as a highly reactive 1-oxido diene, 7 and has been shown to exhibit high diene reactivity in Diels-Alder reactions. For example, Meeks et al reported that anthracenolate ion is condensed with a poor dienophile, ethylene, to give a DielsAlder adduct at high pressure and high temperature, but they did not report any other dienophiles.…”