82855-09-2

Usage

InChI:InChI=1/C18H22O6/c1-21-15-6-5-11(8-14(15)20)7-13(19)12-9-16(22-2)18(24-4)17(10-12)23-3/h5-6,8-10,13,19-20H,7H2,1-4H3/t13-/m0/s1

Upstream product

• 388566-85-6 (E)-5-(2-bromoethenyl)-2-methoxyphenol 
• 388566-84-5 (Z)-5-(2'-bromoethenyl)-2-methoxyphenol 
• 108-95-2 phenol 
• 177329-70-3 (S)-1-(3,4,5-trimethoxyphenyl)-2-(p-toluenesulfonyloxy)ethanol 
• 177329-69-0 (S)-1-(3,4,5-trimethoxyphenyl)-1,2-ethanediol 
• 177472-80-9 (2S)-2-(3,4,5-trimethoxyphenyl)oxirane 
• 177329-71-4 5-Bromo-1-(tert-butyldimethylsilyloxy)-2-methoxybenzene 
• 86-81-7 3,4,5-trimethoxy-benzaldehyde 
• 37942-01-1 5-bromo-2-methoxyphenol 
• 13400-02-7 3,4,5-trimethoxy styrene 
• 97315-21-4 (R)-2-(3-tert-butyldimethylsilyloxy-4-methoxy)phenyl-1-(3,4,5-trimethoxyphenyl)ethanol 
• 97315-17-8 5-<(tert-butyldimethylsilyl)oxy>-(+/-)-combretastatin 
• 97315-18-9 p-methoxy-m-(tert-butyldimethylsilyloxy)-benzaldehyde 
• 97315-20-3 3-<(tert-butyldimethylsilyl)oxy>-4-methoxybenzyl bromide 

Relevant academic research and scientific papers

Catalytic conjunctive cross-coupling enabled by metal-induced metallate rearrangement

Transition metal catalysis plays a central role in contemporary organic synthesis. Considering the tremendously broad array of transition metal-catalyzed transformations, it is remarkable that the underlying elementary reaction steps are relatively few in

Materials and methods for synthesizing stilbenes

The present invention relates materials and methods for synthesizing stilbenes, and in particular to processes for the synthesis of substituted stilbenes such as combretastatin A4. The present invention relates in particular to methods which are stereoselective for either the cis or the trans isomer of the substituted stilbene, using a Perkin-type condensation of an arylacetic acid and a substituted benzaldehyde, followed by a decarboxylation reaction to produce the substituted cis-stilbenes or a Suzuki-type reaction involving a Z or E-ethenyl halide and a substituted boronic acid in the presence of a palladium catalyst to produce specifically either the Z or E-isomer of substituted stilbenes.

Combrestatin a-1 phosphate and combrestatin b-1 phosphate prodrugs

The present invention relates to the syntheses and structural elucidation of Combretastatin A1-Phosphate Prodrugs and Combretastatin B1-Phosphate Prodrugs and the utilization of those prodrugs in the treatment of neoplastic diseases. The prodrugs described herein have the structure: Combretastin A-1 Phosphate Prodrug (I) and Combretastin B-1 Phosphate Prodrug (II).

Efficient method of synthesizing combretastatin A-4 prodrugs

Methods of synthesizing a phosphate ester of combretastat-in A-4 and trans-isomers thereof in which combretastatin A-4 is reacted with dibenzylphosphite in the presence of carbon tetrabromide, or with 2,2,2-trichloroethyl phosphorodichloridate, to form a phosphate ester of combretastatin A-4 with protecting groups thereon.

Enantioselective synthesis of natural combretastatin

In a process which appears to be general for the enantioselective synthesis of oxysubstituted 1,2-diarylethanols, a 4-methoxy-3-silyloxyphenyllithium, obtained by bromine-lithium exchange from the corresponding aryl bromide and t-butyllithium, added selectively at the b-carbon of (S)-2,3,4-trimethoxyphenyloxirane, elaborated from the corresponding styrene via Sharpless asymmetric dihydroxylation, to afford an adduct from which natural (-)-combretastatin was obtained by desilylation.

Combretastatin A-4

The African tree Combretum caffrum (Combretaceae) has been found to contain an agent which is a powerful inhibitor of tubulin polymerization (IC50 2-3 μM), the growth of murine lymphocytic leukemia (L1210 and P388 with ED50 0.003 mg/ml and human colon cancer cell lines (e.g. VoLo with ED50 0.01 μg/ml). This agent is herein denominated ""combretastatin A-4"". The structure assigned by spectral techniques was confirmed by synthesis.

Cell growth inhibitory macrocyclic lactones denominated Combretastatin D-1 and Combretastatin D-2

The isolation and elucidation of novel caffrane macrocyclic lactones denominated "Combretastatin D-1" and "Combretastatin D-2", each of which was found to possess unexpected cell growth inhibitory properties. The lactones have the structural formula: STR1 wherein: STR2