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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 regioselective reaction (minimum:95:5) is used as the key step in a short synthesis of daunomycinone (2a), 2-methoxy-7-deoxycarminomycinone (22b),gamma-rhodomycinone (8), and 10-deoxy-gamma-rhodomycinone (9).The products of the addition of 15 to 4a and 4b, the pseudoacids 16 are converted via the olefins 17 and the epoxides 18 into the ketones 19, which lead by application of known reactions to the anthracyclinones 2a, 22a, and 9.The product, formed by addition of 33 to 4a, is converted to gamma-rhodomycinone (8) via the quinone 27.The precursors of the Grignard reagents 15 and 33, the bromides 14 and 32, can be prepared easily and in large scale from the carboxylic acid 10, which is readily available from the cheap chemicals hydroquinone and succinic anhydride.

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Reference:
Benzofuran – Wikipedia,
Benzofuran | C8H2865O – PubChem

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9-Aminonaphthacene derivative having the formula: STR1 wherein R1 and R2 are both hydrogen atoms or either one of them is a hydrogen atom and the other is hydroxy group or methoxy group; R3 is acetyl group or 1-hydroxyethyl group; R4 is a hydrogen atom; R5 is a hydrogen atom, hydroxy group, lower alkanoyloxy group, amino group, halogen-substituted lower alkanoylamino group or morpholino group; R6 is a hydrogen atom, hydroxy group, lower alkanoyloxy group or tetrahydropyranyloxy group; R7 is a hydrogen atom or methyl group; R is a hydrogen atom; and n is zero or one, which is useful as anti-cancer chemical agents with lower toxicity and with little local irritation and is able to orally be applied.

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Reference:
Benzofuran – Wikipedia,
Benzofuran | C8H2853O – PubChem

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A study by NMR spectroscopic methods and trapping experiments of the mechanism of Wittig reactions between stabilized phosphoranes and unsymmetrically substituted cyclic anhydrides suggests that two reactions are involved: (1) a low-energy, reversible formation of acyclic adducts; and (2) a higher energy “Wittig olefination” reaction leading to enollactones.The latter, more selective, transformation requires a more highly organized transition state in which ?-stacking and stabilizing complexations are important factors.

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Reference:
Benzofuran – Wikipedia,
Benzofuran | C8H2874O – PubChem

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Disclosed are novel compounds, novel compositions, methods of their use, and methods of their manufacture, where such compounds of Formula 1 are pharmacologically useful inhibitors of Protein Tyrosine Phosphatases (PTPases) such as PTP1B, CD45, SHP-1, SHP-2, PTPalpha, LAR and HePTP or the like, wherein n, m, X, Y, R1, R2, R3, R4, R5 and R6 are defined more fully in the description. The compounds are useful in the treatment of type I diabetes, type II diabetes, impaired glucose tolerance, insulin resistance, obesity, and other diseases.

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Reference:
Benzofuran – Wikipedia,
Benzofuran | C8H2844O – PubChem

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The invention provides a compound for use in medicine, the compound being a compound of the formula (VI0) or a salt, solvate, tautomer or N-oxide thereof: wherein the bicyclic group: is selected from the structures C1, C5 and C6: wherein n is 0, 1, 2 or 3; R1 is hydrogen, hydroxy, or O?Rz; R2a is hydroxy, methoxy or O?Rz; provided that at least one of R1 and R2a is O?Rz; Rz is Lp-Rp1; SO3H; a glucuronide residue; a mono-, di- or tripeptide residue; or Lp is a bond, C=O, (C=O)O, (C=O)NRp1 or S(O)xNRp1; x is 1 or 2; Rp1 is hydrogen or a an optionally substituted C1-25 hydrocarbyl group containing 0, 1 or 2 carbocyclic rings and 0, 1, 2, 3, 4, 5 or 6 carbon-carbon multiple bonds, provided that Rp1 is not hydrogen when Lp is a bond, C=O or (C=O)O; and provided also that O?Rz does not contain an O?O moiety; and excluding compounds wherein R1 is hydroxy and R2a is methoxy; Rp2 and Rp3 are the same or different and each is a group Rp1; and R3, R4a, R8 and R10 are defined in the claims. The compounds of formula (VI0) are pro-drugs of parent compounds wherein R1 and/or R2a are hydroxy, wherein the parent compounds have Hsp90 inhibiting activity.

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Reference:
Benzofuran – Wikipedia,
Benzofuran | C8H2846O – PubChem

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A simple and convenient synthesis of 3-methoxyphthalic anhydride by a two-step synthesis involving Diels-Alder reaction of 2-methoxyfuran with maleic anhydride is reported.

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Benzofuran – Wikipedia,
Benzofuran | C8H2879O – PubChem

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The invention provides the use of a compound for the manufacture of a medicament for the treatment of pain, wherein the compound is a compound of the formula (Vl): or a salt, solvate, tautomer or N-oxide thereof; wherein the bicydic group: is selected from the structures C1, C5 and C6: wherein n, R1, R2a, R3, R4a, R8 and R10 are as defined in the claims. The invention also provides the use of a compound of the formula (Vl) for the manufacture of a medicament for the prophylaxis or treatment of a fungal, protozoal, viral or parasitic disease state or condition (other than a disease state or condition due to Plasmodium falciparum) or for use in the prophylaxis or treatment of Ewing’s sarcoma, atherosclerosis or lupus erythematosus

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Reference:
Benzofuran – Wikipedia,
Benzofuran | C8H2856O – PubChem

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Tilivalline 1, a metabolite from Klebsiella pneumoniae var. ocytoca, was easily synthesized in five steps from (S)-proline and 3-(benzyloxy)isatoic anhydride 4g. This synthesis is based on modified Curtius reactions of 3- substituted phthalic anhydrides 11 to 3-substituted isatoic anhydrides 4, conversion of lactams 6 to the acyliminium precursors 7 and stereoselective introduction of indole from the less hindered side of 7.

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Reference:
Benzofuran – Wikipedia,
Benzofuran | C8H2878O – PubChem

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The regioselectivity in the addition of the grignard reagents 5a and 6a to the anhydrides 1 and 2 is determined by the solvent system: in a highly selective manner (3:97), the meta carbonyl group is attacked in tetrahydrofuran/tetramethylethylenediamine, while predominant, but relatively unselective (maximum 78:22) addition to the ortho carbonyl group is observed in diethyl ether.The influence of the solvent system on the regioselectivity is discussed.The LUMO-coefficients of the carbonyl carbon atoms in 1 and 2 were calculated.

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Reference:
Benzofuran – Wikipedia,
Benzofuran | C8H2866O – PubChem

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A problem of 3-methoxyphthalide reduction by metal hydrides was reinvestigated. Various effects controlling selectivity of reductions in 3-substituted phthalides were studied, and a qualitative interpretation of the results is now proposed. Methods for obtaining enhanced yields of one or the other lactonic product were developed.

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Reference:
Benzofuran – Wikipedia,
Benzofuran | C8H2883O – PubChem