100064-16-2

Upstream product

• 75964-00-0 1,4,8-Trihydroxy-2-[3-hydroxy-3-(1-oxo-1λ⁴-[1,3]dithian-2-yl)-pentyl]-anthraquinone 
• 75963-99-4 3-<3-(1,3-Dithian-2-yl)-3-hydroxypentyl>-1,4,5-trihydroxy-9,10-anthrachinon 
• 75963-93-8 4-Hydroxy-3-hydroxymethyl-1,5-dimethoxy-9,10-anthrachinon 
• 75963-95-0 2-(9,10-Dihydro-4-hydroxy-1,5-dimethoxy-9,10-dioxo-3-anthrylmethyl)-3-oxovaleriansaeure-ethylester 
• 75963-96-1 4-Hydroxy-1,5-dimethoxy-3-(3-oxopentyl)-9,10-anthrachinon 
• 75963-98-3 1,4,5-Trihydroxy-3-(3-oxopentyl)-9,10-anthrachinon 
• 75963-94-9 3-Chlormethyl-4-hydroxy-1,5-dimethoxy-9,10-anthrachinon 
• 75963-92-7 4-Hydroxy-1,5-dimethoxy-9,10-anthrachinon 
• 75964-01-1 3-<3-(Dimethoxymethyl)-3-hydroxypentyl>-1,4,5-trihydroxy-9,10-anthrachinon 
• 88100-91-8 (RS)-2-(3-Dichlormethyl-3-hydroxypentyl)-1,4,8-trihydroxy-9,10-anthrachinon 
• 115860-91-8 2-Ethyl-2-hydroxy-4-(1,4,8-trihydroxy-9,10-dioxo-9,10-dihydro-anthracen-2-yl)-butyraldehyde 
• 83923-01-7 2-ethyl-5,8-dimethoxy-7-bromo-1-tetralone 
• 77199-93-0 7-Bromo-2-ethyl-5,8-dimethoxy-1,2,3,4-tetrahydro-naphthalen-1-ol 
• 77199-89-4 2-bromo-7-ethyl-5,6-dihydro-1,4-dimethoxynaphthalene 

Downstream Products

• 63640-62-0 (+/-)10-deoxy-γ-rhodomycinone 
• 5012-65-7 β-Rhodomycinone 

Relevant academic research and scientific papers

A REGIOSELECTIVE SYNTHESIS OF DAUNOMYCINONE AND RELATED ANTHRACYCLINONES.

The phthalic anhydrides 4a and 4b are attacked by the Grignard reagents 15 and 33 in tetrahydrofuran/tetramethylethylene diamine almost exclusively at the carbonyl group, which is situated in the meta position of the methoxy substituent(s).This highly reg

SYNTHETIC ANTHRACYCLINONES-XXVII. ANTHRACYCLINONES BY INTRAMOLECULAR MARSCHALK REACTION. SYNTHESIS OF THE FEUDOMYCINONES AND RHODOMYCINONES.

1,4,5-Trihydroxy-9,10-anthraquinone is transformed regioselectively to the α-hydroxy dichlorides 18-21, which are cyclized to yield predominantely the naturally configurated 9,10-trans-diols 1,3,26, and 27 (80 to 96percent d.e.).The monotrifluoroacetates 38-40 derived from the trans-diols are hydroxylated via bromination at C-7 to yield almost exclusively the 7,9-cis-9,10-trans-triols α1-rhodomycinone (4), feudomycinone D (7), and 4-O-methyl-β-rhodomycinone (42).The feudomycinones A (5) and C (6) are obtained with less chemo- and stereoselectivity by hydroxylation of the 10-deoxycompounds 33 and 34.

Synthetic Anthracyclinones, XXII. - Rhodomycinones of Type A with Methyl, Ethyl, and n-Propyl Side Chain

The anthraquinone derivatives 7, 8, 37, 39, and 40 are prepared by addition of dichloromethyllithium to the corresponding ketones 4, 5, 32b, 34b, and 36b.They can be hydrolized to intermediate aldehydes, which cyclize after reduction to anthracyclinones of Type A with methyl group (11, 12a, 13a, 45, 46a, 47a), ethyl group (15a, 16a, 48, 49, 50a), and n-propyl side chain (51a, 52a).The cis/trans ratio of the 7,8-Diols is approximately 1 : 3.The hydroxy groups at C-10 are introduced stereoselectively to the 8,10-cis-diols 20b, 24, 25a, 53, 54, and 55 via bromination and hydrolysis of the bromides.

REGIOSELECTIVE SYNTHESE VON DAUNOMYCINON UND γ-RHODOMYCINON

Synthesis of daunomycinone (2) and γ-rhodomycinone (3) by regioselective addition of the Grignard reagents 9b and 9d to the anhydride 4.