67122-26-3

Usage

Uses

Used in Pharmaceutical Synthesis:
5,12-Naphthacenedione, 8-acetyl-7,8,9,10-tetrahydro-6,11-dihydroxyis used as a reactant in the synthesis of idarubicinone-7-β-D-glucuronides. This process involves the glucuronidation of idarubicinone with D-glucuronic acid as a key step. Idarubicinone-7-β-D-glucuronides are important intermediates in the production of idarubicin, a potent anthracycline antibiotic with significant anticancer properties. The use of 5,12-Naphthacenedione, 8-acetyl-7,8,9,10-tetrahydro-6,11-dihydroxyin this synthesis process highlights its potential as a valuable building block in the development of pharmaceutical compounds.

Upstream product

• 17648-03-2 9,10-Dihydroxy-2,3-dihydro-anthracene-1,4-dione 
• 116612-01-2 4-Bromo-2-(2-methyl-[1,3]dioxolan-2-yl)-butyraldehyde 
• 78-94-4 methyl vinyl ketone 
• 77422-59-4 2,3-bis(bromomethyl)-1,4-dihydroxyanthracene-9,10-dione 
• 139260-56-3 leuco-2-(3'-oxo-n-butane)quinizarin 
• 106-93-4 ethylene dibromide 
• 69960-30-1 2-(3'-oxo-n-butane) quinizarin 
• 608-43-5 2,3-dimethyl-1,4-dihydroxybenzene 
• 24108-29-0 3-(2-methyl-[1,3]dioxolan-2-yl)-propionaldehyde 
• 89023-98-3 3,10-Dihydroxy-1,2-dihydro-cyclobuta[b]anthracene-4,9-dione 
• 60732-17-4 2,5-dimethoxybenzyl bromide 
• 85-44-9 phthalic anhydride 
• 33654-68-1 2-acetyl-5,8-dimethoxy-1,2,3,4-tetrahydronaphthalene 
• 108440-66-0 2-(4'oxoketal-n-pentane) quinizarin 

Downstream Products

• 84499-12-7 8-Acetyl-6,11-dihydroxy-naphthacene-5,12-dione 
• 709640-12-0 3-acetyl-3,5,12-trihydroxy-6,11-dioxo-1,2,3,4,6,11-hexahydro-1-naphthacenyl 2-(acetyloxy)-2-phenylethanoate 
• 709640-13-1 3-acetyl-3,5,12-trihydroxy-6,11-dioxo-1,2,3,4,6,11-hexahydro-1-naphthacenyl 2-(acetyloxy)-2-phenyl ethanoate 

Relevant academic research and scientific papers

Facile total syntheses of idarubicinone-7-β-D-glucuronide: Convenient preparations of AB-ring synthon using some carboxylic acid derivatives

Regiospecific syntheses of idarubicinone coupled with D-glucuronic acid are described. Cyclization of dimethoxybenzene with carboxylic acid derivatives in polyphosphoric acid (PPA) in one step afforded the naphthalenones 7, which were transformed to the (

Marschalk reaction approaches for the synthesis of (+/-)-4-demethoxydaunomycinone

Marschalk reaction on leucoquinizarin (10) with the appropiate aldehydes 6 or 8 affords the alkylated quinizarin derivatives 11b and 13b respectively which are succesfully elaborated to 4-demethoxy-7,9-dideoxydaunomycinone (4) Marschalk reaction of 10 with bromoaldehyde 9, directly gives 4. 2-Formylquinizarin (21) and levulinic aldehyde 7 under the Marschalk reaction gives 8-acetyl-6,11-dihydroxy-9,10-dihydro-5,12-naphthacenedione (22), a useful intermediate for the asymmetric synthesis of (-)-4-demethoxy-7-deoxydaunomycinone.

4-BROMO-2-ACETOKETAL-1-BUTYLALDEHYDE: AN ELEGANT KEY INTERMEDIATE FOR THE SYNTHESIS OF 4-DEMETHOXY-7,9-DIDEOXYDAUNOMYCINONE BY MARSCHALK REACTION

Marschalk reaction of leucoquinizarin (2) with readily obtainable 4-bromo-2-acetoketal-1-butyraldehyde (3), from ethyl acetoacetate or acetone, gave in one step 4-demethoxy-7,9-dideoxydaunomycinone (1a) in 60percent yield.

A Simple Synthesis of (+/-)-4-Demethoxydaunomycinone

Cycloaddition of 2-acetyl-1,2,3,4-tetrahydro-5,8-naphthoquinone (III) to 1,3-dihydro-1,1-diethoxyisobenzofuran (II) gives a mixture of regioisomeric quinones (IVa and IVb), which on reductive methylation, followed by chromium trioxide oxidation affords (+/-)-4-demethoxy-7,9-dideoxydaunomycinone dimethyl ether (VI).Demethylation, followed by 7,9-hydroxylation of VI furnishes the desired (+/-)-4-demethoxydaunomycinone (Ib).

Studies related to Anthracyclines. Part 2. Synthesis of (+/-)-4-Demethoxydaunomycinone

A chromatography-free, six-step, diastereocontrolled synthesis of (+/-)-4-demethoxy-7-O-methyldaunomycine (3b) is described.The tetracyclic carbon skeleton is elaborated by a Diels-Alder strategy in which the 6a,7 and 10,10a bonds are constructed, the epoxytetraone (5) and the diene (10a) serving as precursors.Hydrolysis of the cycloadduct (11a) leads to the epoxypentaone (12a), the structure of which is confirmed by X-ray crystallography.The diastereocontrol is achieved in the reaction of the dihydroxytrione (13a) with ethynylmagnesium bromide or lithium acetylide, the reagents attacking the 9-carbonyl group from the face away from that bearing the 7-methoxy group to give the ethynyldione (14a).Although epimerisation of the dihydroxytrione (13a) at the 10a-position is a competing reaction when high concentrations of the metal acetylides are employed, the ethynyldione produced, i.e. (20), still possess the trans arrangement of the 7-methoxy and 9-ethynyl groups.The ethynyldiones (14a) and (20) are converted into compound (3b) by an oxidative isomerisation-hydration sequence.An attempt to effect the de-O-methylation of compound (3b), by the action of trimethylsilyl iodide, failed; a mixture of 4-demethoxy-7-deoxydaunomycinone (22b) and its 9-deoxy derivative (22a) resulted.The conversion of compound (3b) into the title compound (3a) is brought about by a trifluoroacetolysis-ammonolysis sequence.The conformation of the A ring of the anthracyclinones (3a) and (3b) and their precursors, as determined by high-field 1H n.m.r. spectroscopy, is discussed.

1,2-Dihydro-3,10-dihydroxycyclobut[b]anthracene-4,9-dione, a key intermediate for 4-demethoxyanthracyclinones

The title compound synthesized in four steps from bicyclo[4.2.0]octane-2,5-dione and o-phthaldehyde undergoes cleanly thermolytic intermolecular Diels-Alder reactions providing a general synthesis of 7,8,9,10-tetrahydro-6,11-dihydroxy-5,12-naphthacenedino