53254-89-0Relevant academic research and scientific papers
Intramolecular aldol-type condensation between side chains of naphthoquinones: Biomimetic synthesis of 1,6- and 1,8-dihydroxyanthraquinones
Uno, Hidemitsu,Masumoto, Akane,Honda, Erina,Nagamachi, Yumi,Yamaoka, Youtarou,Ono, Noboru
, p. 3189 - 3197 (2007/10/03)
Intramolecular condensation of 2-(acetonyl)-3-acyljuglone derivatives under basic conditions gave 1,6- and/or 1,8-dihydroxyanthraquinones depending on the conditions employed. Treatment of 6-[(3-acetyl-5-methoxy-1,4-dioxo-1,4-dihydro-2-naphthyl)methyl]-2,2- dimethyl-4H-1,3-dioxin-4-one with K2CO3 in alcohol brought about the intramolecular Knoevenagel-type reaction to give 3-hydroxy-8-methoxy-1-methyl-9,10-dioxo-9,10-dihydro-anthracene-2- carboxylates in good yields, while the same naphthoquinone gave 4-hydroxy-5-methoxy-9,10-dioxo-9,10-dihydroanthracene-2-acetic acid in good yield by treatment with potassium bis(trimethylsilyl)amide (KHMDS). Chrysophanol, aloe-emodin, aloesaponarin I, and K1115A were prepared in good yields.
Regioselective preparation of 1,6- and 1,8-dihydroxy-9,10-anthraquinones from the common intermediates: Synthesis of aloesaponarin I and K1115A
Uno, Hidemitsu,Nagamachi, Yumi,Honda, Erina,Masumoto, Akane,Ono, Noboru
, p. 1014 - 1015 (2007/10/03)
Treatment of 3-acyl-2-[(2,2-dimethyl-6-oxo-1,3-dioxin-4-yl)methyl]-5-methoxy-1,4-naphthoquino nes with K2CO3 in an alcohol brought about the intramolecular condensation to give 1-alkyl-3-hydroxy-8-methoxy-9,10-anthraquinone-2-carboxy-lates in good yields, while the same naphthoquinone gave 1-hydroxy-8-methoxy-9,10-anthraquinone-3-acetic acid in good yield by treatment with KHMDS.
The synthesis of kermesic acid and isokermesic acid derivatives and of related dihydroxyanthraquinones
Bingham, Stephen J.,Tyman, John H. P.
, p. 3637 - 3642 (2007/10/03)
Cochinellic anhydride methyl, ethyl and benzyl esters (4-methoxy-4-ethoxy- and 4-benzyloxy-carbonyl-5-hydroxy-3-methylphthalic anhydrides) have been prepared by a single stage Diels-Alder reaction of 2-bromomaleic anhydride with 3-alkoxycarbonyl-2,4-bis(trimethylsilyloxy)penta-1,3-dienes. The corresponding 5-methyl ether ethyl ester has been obtained by a similar addition reaction but with 3-ethoxycarbonyl-2-methoxy-4-trimethylsilyloxypenta-1,3-diene. The synthesis of methyl 6-deoxykermesate by the acylation of 1,4-dimethoxybenzene in the presence of boron trifluoride-diethyl ether with cochinellic anhydride methyl ester is unsuccessful. The preferred route is by the Diels-Alder addition of 3-alkoxycarbonyl-2,4-bis(trimethylsilyloxy)penta-1,3-dienes to naphthazarin (or 2-chloronaphthazarin). Lead tetraacetate oxidation of methyl 6-deoxykermesate affords a bis(quinone), Thiele acetoxylation of which gives after hydrolysis and permethylation, a mixture of derivatives of kermesic and isokermesic acids in equal proportions. The Diels-Alder addition of 3-chlorojuglone and 3-alkoxycarbonyl-2,4-bis(trimethylsilyloxy)penta-1,3-dienes has led to an improved synthesis of aloesaponarin-I (3,8-dihydroxy-2-methoxycarbonyl-1-methylanthra-8,10-quinone), while juglone itself affords an isomer which may be the 3,5-dihydroxy compound.
Chemistry of the Coccoidea. VIII. Synthesis of the Ancient Dyestuff Kermesic Acid and of Related Anthraquinones
Cameron, Donald W.,Deutscher, D. Jeanne,Feutrill, Geoffrey I.,Griffiths, Peter G.
, p. 2401 - 2421 (2007/10/02)
The insect anthraquinones kermesic acid (3) and laccaic acid D (2) have been synthesized efficiently, as have the plant anthraquinones aloesaponarin-I (4) and -II (33).The syntheses were based on regiospecific Diels-Alder addition of the silyloxy dienes (10) and (11) to simpler quinones.Regiospecificity was controlled by 2(3)-chloro groups in the dienophiles or, for addition to certain naphthoquinones, by a hydroxy group peri to carbonyl.
