Orientation in Aromatic Substitution. I. 1,2-Dimethoxy-3-isopropylbenzene and 3,5-Dimethylanisole

Edwards, J. D.; Cashaw, Jesse L.

doi:10.1021/ja01596a071

Cited by 23 publications

(9 citation statements)

References 2 publications

(2 reference statements)

Supporting

Mentioning

Contrasting

Order By: Relevance

“…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.…”

mentioning

confidence: 99%

Synthesis of hemigossypol and its derivatives

Wei

Jagt

Royer

et al. 2010

Tetrahedron Letters

View full text Add to dashboard Cite

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.

show abstract

mentioning

confidence: 99%

Synthesis of hemigossypol and its derivatives

Wei

Jagt

Royer

et al. 2010

Tetrahedron Letters

View full text Add to dashboard Cite

show abstract

“…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.…”

mentioning

confidence: 99%

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

Royer

Deck²,

Jagt³

et al. 1995

J. Med. Chem.

View full text Add to dashboard Cite

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.

show abstract

“…2-Bromo-3-methyl-5-methoxybenzyl Alcohol, 2. A mixture of 4-bromo-3,5-dimethylanisole ( 1 ) (86 g, 0.4 mol), N -bromosuccinimide (71.2 g, 0.4 mol) and AIBN (0.2 g) was refluxed in CCl 4 (500 mL) for 4 h. The cooled reaction mixture was washed with sat. NaHCO 3 , dried (MgSO 4 ), and filtered, and the solvent was evaporated to give crude 2-bromo-5-methoxy-3-methylbenzylic bromide as a yellow solid (117.2 g, 85% yield determined by 1 H NMR) which was used in the next step without further purification.…”

Section: Methodsmentioning

confidence: 99%