7414-92-8

Usage

Definition

ChEBI: A member of the class of tetraphenes that is tetraphene-7,12-dione substituted by hydroxy groups at positions 1 and 8 and a methyl group at position 3.

InChI:InChI=1/C19H12O4/c1-9-7-10-5-6-12-17(15(10)14(21)8-9)19(23)11-3-2-4-13(20)16(11)18(12)22/h2-8,20-21H,1H3

Upstream product

• 7351-08-8 tetrangomycin 
• 346605-71-8 8-hydroxy-1-methoxy-3-methylbenz[a]anthracene-7,12-dione 
• 195314-47-7 2-bromo-4-methoxy-1-(methoxymethoxy)-benzene 
• 110451-90-6 (2-bromo-5-methoxy-3-methylphenyl)methanol 
• 7414-94-0 1,8-dimethoxy-3-methylbenz[a]anthracene-7,12-dione 
• 21418-04-2 5-hydroxy-8-methoxy-1,4-naphthoquinone 
• 1362209-53-7 trifluoromethanesulfonic acid 4-bromo-1,8-dimethoxy-3-methyl-7,12-dioxo-7,12-dihydrobenz[a]anthracen-11-yl ester 
• 1362209-50-4 4-bromo-11-hydroxy-1,8-dimethoxy-3-methylbenz[a]anthracene-7,12-dione 
• 1362209-16-2 2-bromo-5-methoxy-1-methyl-3-vinylbenzene 
• 1308649-72-0 2-bromo-5-methoxy-3-methylbenzaldehyde 
• 139462-13-8 1-[5,10-Bis-methoxymethoxy-2-(2-methyl-[1,3]dithiolan-2-ylmethyl)-anthracen-1-yl]-ethanone 
• 139462-12-7 1,8-Bis-methoxymethoxy-3-(2-oxo-propyl)-naphthalene-2-carbaldehyde 
• 130519-94-7 methyl 3-(3-tert-butoxycarbonyl-2-oxopropyl)-1,8-dihydroxynaphthalene-2-carboxylate 

Downstream Products

• 85178-50-3 1-Hydroxy-8-methoxy-3-methylbenzanthracene-7,12-dione 

Relevant academic research and scientific papers

Total synthesis of antibiotic C104: Benzyne-Furan cycloaddition approach to the angucyclines

First total synthesis of antibiotic C104 (1), a prototypical member of the angucyclines, was accomplished. Highly regioselective cycloaddition of α-alkoxybenzyne 12 with angularly fused α-siloxyfuran 10 enabled the straightforward construction of the char

A general approach to angucyclines: Synthesis of hatomarubigin A, rubiginone B2, antibiotic X-1488E, 6-hydroxytetrangulol, and tetrangulol

Hatomarubigin A was prepared in 41% yield in a single procedure from acyl naphthoquinone 15 and 5-methylcyclohexane-1,3-dione (16). The net reaction consists of Michael addition to an acyl quinone followed by intramolecular aldol condensation. Hatomarubigin A then served as a common intermediate in syntheses of the angucyclinone antibiotics rubiginone B2, antibiotic X-1488E, 6-hydroxytetrangulol, and tetrangulol. (C) 2000 Elsevier Science Ltd.

A general strategy for diverse syntheses of anhydrolandomycinone, tetrangulol, and landomycinone

A general synthetic strategy based on a protecting group-promoted CH arylation method was developed for total syntheses of anhydrolandomycinone (1), tetrangulol (2), and landomycinone (3) from the same set of starting materials.

A unified strategy for the syntheses of angucyclinone antibiotics: Total syntheses of tetrangulol, kanglemycin M, X-14881-E, and anhydrolandomycinone

A unified strategy for the syntheses of angucyclinone antibiotics was developed utilizing sequential intramolecular enyne metathesis, Diels-Alder/aromatization, photooxygenation, and one-pot elimination/ aromatization reactions. The diversity in this sequ

Room-temperature B(OAc)3-promoted diels-alder reaction of juglone with styrenes: Total syntheses of tetrangulol and anhydrolandomycinone

The Diels-Alder reaction of juglone with various styrenes in the presence of 2,3-dichloro-5,6-dicyanobenzoquinone (DDQ) was promoted by B(OAc)3 at room temperature. The reaction proceeded smoothly and gave the products in a good yield and with

Regiochemical control by remote substituents. A direct synthesis of tetrangulol

Diels-Alder reactions of quinones 4 and 10 exhibit remarkable regioselectivity. This selectivity plus a novel phosphazine-mediated cyclization has led to a six-step synthesis of tretrangulol.

Biomimetic-type synthesis of the racemic non-aromatic angucyclinones of the SF 2315 and SS 228Y types

The biomimetic-type aldol reaction of the tricyclic (E)-configured precursors 6a/b gave the racemic nonaromatic angucycline derivatives 11-13 of the SF 2315 and SS 288Y types. Chelate controlled conditions in the cyclization of 6b led to the regioisomeric product 10.

Synthesis of angucyclines. 8. Biomimetic-type synthesis of rabelomycin, tetrangomycin, and related ring B aromatic angucyclinones

The angucyclinones with aromatic ring B (1a-c and 2a-c) are prepared in a biomimetic-type synthesis by two successive aldol cyclizations starting from the substituted naphthoquinones 12a-c. In both cyclization steps the C-H acidity of the potential nucleophilic centers determines the mode of cyclization under kinetically controlled conditions. The tetrahydroanthraquinones 13a-c/14a-c are hydroxylated at C-4 to the phenolic anthraquinones 16a-c upon treatment with excess NMO.

Total Synthesis of Angucyclines, 4. Synthesis of rac-Tetrangomycin

The synthesis of racemic tetrangomycin (11) is reported.In the key step the hexahydrobenzanthraquinone 8 is generated in a regioselective Diels-Alder reaction of diene 5 with bromonaphthoquinone 7.The conversion of 8 into 11 involves only three operati

Biosynthesis of PD 116740: Origins of the carbon, hydrogen, and oxygen atoms and derivation from a 6-deoxybenz[a]anthraquinone

The benz[a]anthraquinone antibiotic PD 116740 is formed from the regular cyclization of a decaketide intermediate folded in a manner to generate the angular tetracyclic skeleton. The 6-deoxybenz[a]anthraquinone tetrangulol is an intermediate, indicating t