Steroid succinic acid

Methyl- 1,3-cyclopentanedione is a key intermediate for the total synthesis of steroids.2 A number of methods have been described for its preparation, among them the condensation of succinic acid with propionyl chloride,3 and that of succinic anhydride with 2-buten-2-ol acetate,4 both in the presence of aluminum chloride. It has also been obtained from 3-methylcyclopentane-1,2,4-trione by catalytic hydrogenation5 and Wolff-Kishner reduction 6 The base-promoted cyclization of 4-oxohexanoic acid ethyl ester and diethyl propionylsuccinate with tertiary alkoxides was first reported by Bucourt.7 The present cyclization process provides an experimentally simple route to 2-methyl-1,3-cyclopentanedione. Using the same procedure, 4-oxoheptanoic acid ethyl ester has been cyclized to give 2-ethyl-l,3-cyclopentanedione in 46% yield... 

Sodium toluene dispersion of, 55, 65 Sodium p-toluenesulfinate, 57, 103 Spiro[4 n] alkenones, 58, 62 Spiro[cyclopentane-l,l -indene] 55, 94 Squalene, 56, 116 Squalene, 2,3-epoxy, 56, 116 Stannic chloride, 56, 97 Steroids synthesis, 58, 85 E Stilbene, 55, 115,58, 73 z-Stilbene, 58, 133 Styrene, 56, 35,58, 43 Styrene glycol, 55, 116 Styrene glycol dimesylate, 55, 116 Succinic acid, 58, 85 Succinic anhydride, 58, 85 Sucunimide, 56, 50, 58, 126 Succimmide, Vbromo, 55, 28, 56, 49 SULFIDE CONTRACTION, 55, 127 Sulfide, dimethyl-, 56, 37 SULFIDE SYNTHESIS, 58, 143,58, 138 SULFIDE SYNTHESIS ALKYL ARYL SULFIDES, 58, 143 SULFIDE SYNTHFSIS DIALKYL SULFIDES, 58, 143 SULFIDE SYNTHESIS UNSYMMETRI-CAL DIALKYL DISULFIDES, 58, 147 SULFONYL CYANIDES, 57, 88 Sulfur tetrafluoride, 57, 51... 

A hybrid compound consisting of structural motifs from des-A steroids and succinic acid led to the design and synthesis of a very potent des-A succinate inhibitor. This compound inhibited rHFPTase (IC50 = 40 nM) and required the VP-methyl group for the potency. While the C-7 unsubstituted compound was only about 5-fold less active, the substitution with larger groups was not tolerated. For example, the succinate with a 7P-ethyl group was 75-fold less active [117]. 

DEG succinate Diethylene glycol succinate 200 Steroids, Amino Acids, Alcohols... 

The spacer can be constructed also using a succinic acid C-4 fragment, coupled at both ends with either OH or NH2 groups, as appropriate on the carbohydrate and steroid (or triterpene) precursors, as in the synthesis of compounds 44-46 (Fig. 11), along with others made in these studies. ... 

The diacylation of isopropenyl acetate with anhydrides of dicarboxylic acids is applicable for the synthesis of several other cyclic jS-triketones in moderate yield. - It has been used for the synthesis of 2-acetylcyclohexane-l,3-dione (40% yield), 2-acetyl-4-methylcyclopentane-l,3-dione (10% yield), 2-acetyl-4,4-dimethylcyclopentane-l,3-dione (10% yield), 2-acetyl-5,5-dimethylcyclohexane-l,3-dione (10% yield), 2-acetylcyclo-heptane-l,3-dione (12% yield) and 2-acetylindane-l,3-dione (26% yield). Maleic anhydrides under more drastic conditions give acetylcyclopent-4-ene-l,3-diones in yields from 5% to 12%. The corresponding acylation of the enol acetate of 2-butanone with succinic anhydride has been used to prepare 2-methylcyclopentane-l,3-dione, an important intermediate in steroid synthesis. - ... 

This class of haptens includes those that have a carboxyl group, such as acetylsalicylic acid (aspirin) or the peptides angiotensin and brady-kinin. In addition, many haptens, such as some steroids, may have reactive groups to which a carboxyl group can be attached as, for example, by reaction with succinic anhydride (see below). For conjugation to proteins, the same procedures may be used regardless of whether the carboxyl group is present as an inherent part of the hapten or as an added moiety. 

Fig. 10. GLC of trimethylsilyl derivatives of synthetic steroid mixture. (A) Procedure using 2% neopentyl glycol succinate on Chromosorb W, acid-washed, dimethyldichlorosilane treated, 80-100 mesh, in 6 foot X 5 mm i.d. glass column at 215° with 10 psi nitrogen. (B) Procedure using 35% XE-60 on Anakrom ABS (90-100 mesh), in 6 foot X 5 mm i.d. glass column, at 232°, with 5 psi nitrogen. Reproduced from Ruchelman and Cole (R4) with permission.

Besides the aforementioned A-ring aromatic steroids and contraceptive agents, partial synthesis from steroid raw materials has also accounted for the vast majority of industrial-scale steroid synthesis. One notable exception, however, was the first industrial-scale synthesis of optically active steroids performed by workers at Roussel-UCLAF. The linear synthesis began with a suitable B—C-ring synfhon, 6-methoxy-l-tetralone (186). In a series of steps, tetralone (186) was converted to 2-methyl-2-cyanotetralone (270). Condensation of (270) with dimethyl succinate followed by carbonyl reduction, saponification, and resolution produced the optically active tricyclic acid (271). A series of reductions, a decarboxylation, and a hydrolysis produced (272). Appendage of the A-ring functionality by alkylation produced intermediate (273). Compound (273) was used as a common intermediate for the synthesis of 19-norsteroids, estrogens, and corticosteroids (230). 

These compounds, occuring mostly in urine or obtained synthetically, are derivatives of androgens, corticosteroid metabolites and oestrogens they are principally sulphate or phosphate esters or glucuronides (combined with glucuronic acid via a jff-glycosidic link). Their separation in column or paper chromatography has been described earlier (cf. [129]). Synthetic acid esters of steroids with succinic or tetrahydrophthahc acids may be classified here also. 

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