Improved Synthesis of 1,2-Dimethoxy-3-Isopropylbenzene and General Synthesis of 3-Substituted-1,2-Dimethoxybenzenes

Deck, Lorraine M.; Brazwell, Eugenia M.; Jagt, David L. Vander; Royer, Robert E.

doi:10.1080/00304949009356311

Cited by 10 publications

(7 citation statements)

References 9 publications

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“…383 In the improved synthesis of 1,2dimethoxy-3-isopropylbenzene and general synthesis of 3substituted 1,2-dimethoxybenzenes, bromination of 2-isopropylphenol with bromine and tert-butylamine in toluene− dichloromethane was carried out to give 89% 2-bromo-6isopropylphenol (Scheme 120). 384 Methylation of the latter compound and then sequential treatment with Mg and BH 3 in THF, and then water, sodium hydroxide, and hydrogen peroxide, followed by methylation, produced 88% 1-isopropyl-2,3-dimethoxybenzene.…”

Section: Bromination Reactions 31 Bromination With Molecular Brominementioning

confidence: 99%

Use of Bromine and Bromo-Organic Compounds in Organic Synthesis

2016

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Bromination is one of the most important transformations in organic synthesis and can be carried out using bromine and many other bromo compounds. Use of molecular bromine in organic synthesis is well-known. However, due to the hazardous nature of bromine, enormous growth has been witnessed in the past several decades for the development of solid bromine carriers. This review outlines the use of bromine and different bromo-organic compounds in organic synthesis. The applications of bromine, a total of 107 bromo-organic compounds, 11 other brominating agents, and a few natural bromine sources were incorporated. The scope of these reagents for various organic transformations such as bromination, cohalogenation, oxidation, cyclization, ring-opening reactions, substitution, rearrangement, hydrolysis, catalysis, etc. has been described briefly to highlight important aspects of the bromo-organic compounds in organic synthesis.

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Section: Bromination Reactions 31 Bromination With Molecular Brominementioning

confidence: 99%

Use of Bromine and Bromo-Organic Compounds in Organic Synthesis

2016

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“…19 The precursor bromides are readily prepared from commercially available starting materials using procedures described in the literature. 20, 21, 22 In some preparations of the bromides using the Edward's procedure 22 small amounts (5 to 10%) of the isomeric bromides 5-bromo-3-alkyl-1,2-dimethoxybenzene were formed. 23 An alternate highly regioselective silica gel catalyzed bromination, using N-bromosuccinimide proved more effective.…”

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confidence: 99%

Synthesis of hemigossypol and its derivatives

Wei

Jagt

Royer

et al. 2010

Tetrahedron Letters

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Hemigossypol (3), a sesquiterpene natural product, was previously isolated from Gossypium barbadense and was shown to display improved anti-fungal activity compared to gossypol (1), the disesquiterpene dimer of hemigossypol (3). Gossypol exhibits multiple biological activities. In order to study whether hemigossypol and it derivatives retain the various bioactivities of gossypol, we developed a short and convenient synthetic scheme to synthesize hemigossypol. This is the first de novo synthesis of this natural product. In addition derivatives of hemigossypol with various 2,5-alkyl substituents were synthesized. Modification of the synthetic scheme also afforded the natural product hemigossylic lactone (4) and its 2,5-substituted derivatives.

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“…readily prepared from commercially available starting materials. [16][17][18] The double bond of ester 8 is difficult to reduce in good yield, so the ester was saponified to form carboxylic acid 9 which was catalytically hydrogenolyzed and reduced in one step. Carboxylic acid 10 was cyclized with polyphosphoric ester according to a published procedure to form 11.…”

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confidence: 99%

“…This was accomplished in 55% yield by treating 14 with nbutyllithium and coupling with C0CI2 catalyst.21 •22 The carbonyl groups were introduced by formylation of 15 with titanium tetrachloride and dichloromethyl methyl ether.23 •24 The aldehyde groups were converted to carboxylic acids by mild oxidation with sodium hypochlorite. 25 The methyl groups were removed from the phenolic ethers of 16 Anti-HIV Activity. Inhibition of replication of H9/ HIV-IIIb in HT46c cells by DDG, DDGA, DHG, and DHGA is shown in Figure 1.…”

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Synthesis and Anti-HIV Activity of 1,1'-Dideoxygossypol and Related Compounds

Royer

Deck²,

Jagt³

et al. 1995

J. Med. Chem.

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1,1'-Dideoxygossypol (DDG), 1,1'-dideoxygossylic acid (DDGA), 8-deoxyhemigossypol (DHG), and 8-deoxyhemigossylic acid (DHGA) were synthesized and tested for their ability to inhibit the replication of HIV in vitro. The EC50 for DDGA was < 1 microM, and its threshold cytotoxicity was approximately 20 microM. DDG was less effective than DDGA against HIV and showed considerable toxicity at 5 microM. DHGA was ineffective against HIV and had very low cytotoxicity. DHG showed some anti-HIV activity, but the threshold cytotoxicity was 5 microM. The dissociation constants for the binding of the four compounds to human serum albumin were determined by fluorescence quenching titrations, and all four were found to have much lower affinities for albumin than the parent compound gossypol.

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Improved Synthesis of 1,2-Dimethoxy-3-Isopropylbenzene and General Synthesis of 3-Substituted-1,2-Dimethoxybenzenes

Cited by 10 publications

References 9 publications

Use of Bromine and Bromo-Organic Compounds in Organic Synthesis

Use of Bromine and Bromo-Organic Compounds in Organic Synthesis

Synthesis of hemigossypol and its derivatives

Synthesis and Anti-HIV Activity of 1,1'-Dideoxygossypol and Related Compounds

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