75716-69-7

Upstream product

• 5765-44-6 5-methylisoxazole 
• 1830-54-2 3-oxopentanedioic acid dimethyl ester 
• 625-34-3 3-oxobutyraldehyde 
• 1809-59-2 4-(diethylamino)-3-butene-2-one 
• 1423-60-5 methyl ethynyl ketone 
• 67-64-1 acetone 
• 2976-86-5 1-amino-1-buten-3-one 
• 1119-19-3 but-2-ynal 

Downstream Products

• 83769-04-4 methyl 8-hydroxy-3-methyl-1-oxo-3,4-dihydro-(1H)-2-benzopyran-7-carboxylate 

Relevant academic research and scientific papers

One pot synthesis of phenolic compounds from aliphatic ones

Synthesis of tetra and pentasubstituted phenols from dimethyl 1,3- acetonedicarboxilate anion 1 and alkinones 2 is described. The salient feature of this procedure is to provide phenols with regiocontrol at the 3/5 positions.

Syntheses of extreme sterically hindered 4-methoxyboronic acids

4-Iodoanisoles 3a,b, 3d and 4-bromoanisoles 4a-d were readily obtained. An extreme steric hindrance precluded obtaining 3c. Catalytic borylation of 3a,b, 3d followed by hydrolysis of boronic ester 26a,b, 26d easily provided the boronic acids 5a,b, 5d. Com

Total synthesis and cytotoxicity evaluation of all ochratoxin A stereoisomers

The mycotoxin ochratoxin A is a potent inhibitor of the protein biosynthesis and known to be cytotoxic in nanomolar concentrations. In order to investigate the relationship between stereochemistry and cytotoxicity of this compound, all four ochratoxin A stereoisomers have been synthesized. Using the liver cell line Hep G2, the compounds were tested for cytotoxic and apoptotic potential. It could be shown, that the l-configuration of the phenylalanine moiety of the molecule is mostly responsible for the high cytotoxicity of ochratoxin A while the stereocenter at the dihydroisocoumarine structure is of less importance.

A new and expedient total synthesis of ochratoxin A and d 5-ochratoxin A

A new total synthesis of the mycotoxin ochratoxin A (OTA) is presented, in which it is prepared in 9% overall yield from commercially available substrates. The key step consists of the condensation reaction between protected L-phenylalanine and 5-chloro-8-hydroxy-3-methyl-1-oxoisochromane-7-carboxylic acid (ochratoxin α, OTα). The same strategy could be successfully applied to L-d5-phenylalanine, leading to the first total synthesis of d5-OTA, a molecular tracer for the detection and analytical quantification of the natural mycotoxin in food samples by means of stable isotope dilution assay (SIDA). Georg Thieme Verlag Stuttgart.

COMPOUNDS AND COMPOSITIONS USEFUL IN THE TREATMENT OF NEOPLASIA

There is described compounds for use in therapy, said compounds being defined by Formula (1): There is also described an anti-proliferative composition comprising one or more compounds according to Formula (1), and a method of treatment of neoplasia comprising the administration of such a compound or composition.

A Convenient One-Pot Method for the Construction of Tetrasubstituted Phenols through a Michael Addition-Aldol Cyclization Sequence

The sodium salt of dimethyl 1,3-acetonedicarboxylate (1) readily reacts with certain alkynals under mild conditions in THF to give a tetrasubstituted aromatic ring with regiocontrol at the metaposition through a Michael addition-aldol cyclization sequence. Thus the reaction of I with propynal, 2-butynal, 2-pentynal, 2-octynal, 4-(benzoyloxy)-2-butynal, and 4-((tetrahydropyranyl)-oxy)-2-butynal at 25 °C gave the following products: dimethyl 2-hydroxybenzene-1,3-dicarboxylate (11percent), dimethyl 2-hydroxy-4-methylbenzene-1,3-dicarboxylate (45percent), dimethyl 4-ethyl-2-hydroxybenzene-1,3-dicarboxylate (46percent), dimethyl 2-hydroxy-4-pentylbenzene-1,3-dicarboxylate (42percent), dimethyl 2-hydroxy-4-((pivaloyloxy)methyl)benzene-1,3-dicarboxylate (88percent), dimethyl 2-hydroxy-4-((benzoyloxy)methyl)benzene-1,3-dicarboxylate (74percent), and dimethyl 2-hydroxy-4-(((tetrahydropyranyl)oxy)methyl)benzene-1,3-dicarboxylate (70percent).

A New Aromatic Annelation Reaction with Two Synthons, Enaminones and 3-Oxoglutarate. Studies on the β-Carbonyl Compounds Connected with β-Polyketides. VIII

Reactions of the enaminones 1 with dimethyl 3-oxoglutarate in the presence of KF-AcOH or AcONa-AcOH and 18-crown-6 gave the dimethyl 2-hydroxy-1,3-benzenedicarboxylates 3, providing a new aromatic annelation reaction.Keywords - enaminone; dimethyl 3-oxoglutarate; buffer catalysis; aromatic annelation; dimethyl 2-hydroxy-1,3-benzenedicarboxylate