Hydroaromatic steroid hormones. IV. (+)-19-Nor-D-Homotestosterone

1955 ◽  
Vol 8 (4) ◽  
pp. 519 ◽  
Author(s):  
AJ Birch ◽  
RJ harrisson
Keyword(s):  
Acid Hydrolysis ◽  
Steroid Hormones ◽  
Methyl Ether ◽  
Liquid Ammonia

(+)-19-Nor-D-homotestosterone (III) has been synthesized by reduction of (+)-D-homo-oestrone methyl ether with lithium and ethanol in liquid ammonia, followed by acid hydrolysis.

Reduction by Dissolving Metals

1955 ◽  
Vol 8 (4) ◽  
pp. 512 ◽  
Author(s):  
AJ Birch ◽  
J Cymerman-Craig ◽  
M Slaytor
Keyword(s):  
Acid Hydrolysis ◽  
Good Yield ◽  
Liquid Ammonia ◽  
The Right

The reduction by sodium and ethanol, with or without liquid ammonia as solvent, of various amidines followed by acid hydrolysis, leads in many cases to a good yield of the corresponding aldehyde. Further reduction in liquid ammonia of several 2-aryl-imidazolines or imidazolidines followed by acid hydrolysis leads to the 2,5-dihydro-benzaldehyde derivative. The reduction of some acid amides by sodium and proton sources in liquid ammonia has been examined. Under the right conditions this process is of preparative value for aldehydes.

Catalytic intramolecular participation of amide group in the acid hydrolysis of methyl ether linkage

Tetrahedron ◽  
1995 ◽  
Vol 51 (35) ◽  
pp. 9729-9736 ◽  
Author(s):  
Antonio Arcelli ◽  
Gianni Porzi ◽  
Sergio Sandri
Keyword(s):  
Acid Hydrolysis ◽  
Methyl Ether ◽  
Amide Group ◽  
Ether Linkage ◽  
Hydrolysis Of

scholarly journals Flavonoid Aglycones and Glycosides from the Leaves of some Japanese Artemisia Species

2018 ◽  
Vol 13 (5) ◽  
pp. 1934578X1801300
Author(s):  
Ayumi Uehara ◽  
Kazuhide Shimoda ◽  
Yoshinori Murai ◽  
Tsukasa Iwashina
Keyword(s):  
Acid Hydrolysis ◽  
Methyl Ether ◽  
The Other ◽  
Flavonol Glycosides ◽  
Flavonoid Aglycones ◽  
Other Hand ◽  
Artemisia Species ◽  
C Nmr

Sixteen Japanese Artemisia taxa were surveyed for flavonoid aglycones and glycosides. The leaves were rinsed with acetone and then extracted with MeOH. Isolated flavonoids were identified by UV, LC-MS, acid hydrolysis, 1H and 13C NMR, and/or HPLC comparisons with authentic samples. Thus, nine flavone aglycones, apigenin (10), luteolin (5), chrysoeriol (11), hispidulin (6), jaseosidin (7), nepetin (15), sudachitin (8), luteolin 7-methyl ether (13) and eupatilin (14), three flavonol aglycones, axillarin (9), quercetin 3-methyl ether (16) and 5,7,4′-trihydroxy-3,6-dimethoxyflavone (12), one flavanone aglycone, pinocembrin (4), three dihydroflavonol aglycones, taxifolin (1), taxifolin 3-acetate (2) and padmatin (3) were found in their Artemisia taxa with the various combination. On the other hand, four flavonol glycosides, quercetin 3- O-rutinoside (17), quercetin 3- O-glucoside (18), patuletin 3- O-glucoside (19) and patuletin 3- O-rhamnosylglucoside (20), were isolated from a few Artemisia taxa.

Preparation of Some 9-Hydroxy-2-oxaspiro[4.5]dec-8-ene-1,7-dione Derivatives by Reductive Alkylation of 3,5-Dimethoxybenzoic Acid With 1,2-Dihaloalkane and Oxiran Electrophiles

1989 ◽  
Vol 42 (8) ◽  
pp. 1207 ◽  
Author(s):  
JS Wilkie ◽  
KN Winzenberg
Keyword(s):  
Carboxylic Acid ◽  
Acid Hydrolysis ◽  
Liquid Ammonia ◽  
Major Product ◽  
Reductive Alkylation

Lithium in liquid ammonia mediated reductive alkylation of 3,5-dimethoxybenzoic acid (3) with 1,2-dibromoethane, or 1-bromo-2-chloroethane, followed by acid hydrolysis, afforded 9-hydroxy-2-oxaspiro[4.5]dec-8-ene-1,7-dione (1a). Reductive alkylation of (3) with unbranched 1,2-dibromoaikanes (5b-g), 1,2-dibromo-3-methylbutane and 1,2-dibromo-3,3-dimethylbutane gave 3-alkyl-9-hydroxy-2-oxaspiro[4.5]dec-8-ene-1,7-dione derivatives (1b-i) in moderate yields with the exception of (1i). The major product of the last reaction was 1-(2-bromo-3,3- dimethylbutyl )-3-hydroxy-5-oxocyclohex-3-ene-1-carboxylic acid (9). No reductive alkylation of (3) was observed with 2,3-dibromobutane or 1,2-dibromo-2methylpropane. Reductive alkylation of (3) with the oxiran derivatives (8a-d) afforded the 2-oxaspiro[4.5]dec-8-ene-1,7- dione derivatives (1a-c,j). Reductive alkylation of (3) with 1,3-dibromopropane and l-bromo-3-chloropropane gave, after hydrolysis, 1-(3-bromopropyl)-3-hydroxy-5-oxocyclohex-3-ene-l- carboxylic acid (12a) and 1-(3-chloropropyl)-3-hydroxy-5-oxocyclohex-3-ene-1-carboxylic acid (12b). The conversion of (1a) into 8-[1-( ethoxyimino )butyl]-9-hydroxy-2-oxaspiro[4.5]dec-8-ene-1,7-dione (2a) is described.

Preparation of aliphatic analogues of S-adenosyl-L-homocysteine and related compounds

1981 ◽  
Vol 46 (12) ◽  
pp. 3134-3144 ◽  
Author(s):  
Antonín Holý
Keyword(s):  
Hydrogen Sulfide ◽  
Acid Hydrolysis ◽  
Sodium Salt ◽  
Liquid Ammonia ◽  
Disodium Salt ◽  
Sodium Hydrogen ◽  
Benzylidene Derivative ◽  
Polymeric Compounds ◽  
Related Compounds

Reaction of 9-((RS)-2,3-dihydroxypropyl)adenine (I) with p-toluenesulfonyl chloride afforded the 3-O-p-toluenesulfonyl derivative II which on treatment with 2,3-dihydropyran was transformed into the 3-O-p-toluenesulfonyl-2-O-tetrahydropyranyl derivative III. Reaction of II with sodium isobutyl mercaptide in liquid ammonia gave 9-((RS)-3-isobutylthio-2-hydroxypropyl)adenine (IV). Analogously, compound III and disodium salt of L-homocysteine after acid hydrolysis afforded S-((RS)-3-(adenin-9-yl)-2-hydroxypropyl)-L-homocysteine (V). 9-((2S,3S)-threo-2,3-O-Isopropylidene-4-O-p-toluenesulfonyl-2,3,4-trihydroxybutyl)adenine (VIII) was transformed in a similar way into the 4-isobutylthio derivative IX and the L-homocysteine derivative X. 9-Allyladenine (XII) on treatment with bromine in dioxane afforded 9-((RS)-2,3-dibromopropyl)adenine (XIII) and probably 3,9-(2-bromotrimethylene)adeninium bromide (XIV). Reaction of compounds XIII, XIV and 9-((RS)-2,3-bis-p-toluenesulfonyloxypropyl)adenine (XI) with sodium hydrogen sulfide or sodium thioacetate led invariably to polymeric compounds. 4-p-Toluenesulfonyloxymethyl-2,2-dimethyl-1,3-dithiolane (XVa) reacted with sodium salt of adenine to give 9-(X)-2,2-dimethyl-1,3-dithiolane-4-ylmethyl)adenine (XVIa); analogously, 4-p-toluenesulfonyloxymethyl-2-phenyl-1,3-dithiolane (XVb) afforded the 2,3-S-benzylidene derivative XVIb and 1-p-toluenesulfonyloxy-2,3-bis(benzylthio)propane (XIXb) gave 9-((RS)-2,3-bis(benzylthio)propyl)adenine (XIXc). Acetolysis of XVIa or reduction of XVIb with sodium in liquid ammonia led to 9-((RS)-2,3-dimercaptopropyl)adenine (XVIII) and the corresponding episulfide XVII.

SYNTHESIS OF 8-AZA-D-HOMO-18-NORESTRONE METHYL ETHER

1965 ◽  
Vol 43 (5) ◽  
pp. 1323-1328 ◽  
Author(s):  
Norman A. Nelson ◽  
Yasumitsu Tamura
Keyword(s):  
Acid Hydrolysis ◽  
Methyl Ether ◽  
Potassium Salt ◽  
Lithium Aluminium Hydride ◽  
Enol Ether ◽  
Hydride Reduction ◽  
Lithium Aluminium ◽  
Similar Series

Alkylation of the potassium salt of 1,4-dihydro-2,6-dimethoxybenzene with 2-(2-bromoethyl)piperidine yielded the bis-enol ether I, which, on acid hydrolysis, afforded the crystalline vinylogous amide II. Lithium aluminium hydride reduction of II gave two isomers of 1,2,3,4,4a,5,6,6a,8,9,10,10a-dodecahydro-7H-benzo[c]quinolizin-7-one (III). A similar series of reactions starting with 1-(2-chloroethyl)-6-methoxy-1,2,3,4-tetrahydroisoquinoline hydrochloride (V) gave two isomers of 2,3,4,4a, 6,7,11b,12,13,13a-decahydro-9-methoxy-1H-di-benzo[a,f]quinolizin-1-one (8-aza-D-homo-18-norestrone methyl ether) (IX).

Steroid hormones. XXI. Some testosterone derivatives substituted at C19

1970 ◽  
Vol 23 (2) ◽  
pp. 341 ◽  
Author(s):  
AJ Birch ◽  
B McKague
Keyword(s):  
Steroid Hormones ◽  
Methyl Ether ◽  
Isoprene Unit ◽  
Alcohol Mixture ◽  
Methylmagnesium Iodide ◽  
Ring Fission ◽  
Similar Series ◽  
Derivatives Of

Addition of but-1-en-3-one to (1) produced the adducts (28) and (2b) which undergo ring fission with acid to give (3). Methylmagnesium iodide on (2a) and (2b) gives the alcohol mixture (4) which is converted by acid into (5). A similar series of reactions with derivatives of l,2-dihydrooestrone methyl ether gives the steroid (10) and the 17β-OH analogue, and (11) containing an angular isoprene unit.

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