- Preparation of 2-(6-carboxyhexyl)- and 2-(6-methoxycarbonylhexyl)cyclopent-2-en-1-one using free radical reactions
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Two short and simple synthetic routes to the prostaglandin synthons 2-(6-carboxyhexyl)- and 2-(6-methoxycarbonylhexyl)cyclopent-2-en-1-one have been developed. The first is based on a cyclohexanone oxidative transformation with hydrogen peroxide and di-tert-butyl peroxide, the second on the free radical addition reaction of methyl 9-oxononanoate to acrylaldehyde diacylal.
- Ogibin,Starostin,Aleksandrov,Pivnitsky,Nikishin
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p. 901 - 903
(2007/10/02)
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- MICROBIOLOGICAL SYNTHESIS OF S(-)-2-(4-CARBOXY-3-HYDROXYBUTYL)-2-CYCLOPENTEN-1-ONE AND SOME OF ITS PROPERTIES
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A microbiological synthesis of S(-)-2-(4-carboxy-3-hydroxybutyl)-2-cyclopenten-1-one was undertaken.Its methyl ether undergoes enantiospecific cyclization to 2-methoxycarbonylmethyl-5-oxocyclopentatetrahydropyran with the total asymmetric induction of two new S-chiral centers.The chiroptical characteristics of the compounds are examined.
- Freimanis, Ya. F.,Milman, I. A.,Matysova, G. R.,Liepin'sh, E. E.
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p. 1696 - 1703
(2007/10/02)
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- A New Synthesis of 8-(ω-Carbomethoxyhexyl)-11-hydroxycyclopent-8(12)-ene-9-one, a Versatile Prostaglandin Intermediate
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8-(ω-Carbomethoxyhexyl)-11-hydroxycyclopent-8(12)-ene-9-one (V), a versatile prostaglandin synthon, has been synthesised starting from easily accesible undecylenic acid (VI).The synthesis involves preparation of dihydroxy undecanoic acid (IX) and its methyl ester (X), methyl 9-formylnonanoate (XI), the monoester (XII) and the corresponding unsaturated acid (XIII), γ-lactone (XIV), cyclopentenone acid (XV) and finally the all important PG-intermediate 2-(ω-carbomethoxyhexyl)cyclopentenone (IV).Its reduction with sodium borohydride gives the saturated alcohol (XVI), which via oxidation with Jones' reagent and bromination-dehydrobromination sequence could be converted back to IV.However, IV, on reduction with aluminium isopropoxide gives the allylic alcohol (XXIII), which is converted via acetylation into the acetate (XXIV).Subsequent oxidation of acetate (XXIV) with t-butyl chromate yields the keto-acetate (XXV), which on reduction with aluminium isopropoxide furnishes the hydroxy acetates (XXXII).The hydroxyl group in XXXII is protected as tetrahydropyranyloxy derivative (XXXIII).Hydrolysis of XXXIII with alkali leads to the hydroxy acids (XXXIV).Oxidation of XXXIV with Jones' reagent at low temperature for a short period yields the keto-acid (XXXV), which is esterified to give the ester (XXXVI).Finally, removal of the pyranyloxy group from XXXVI furnishes the versatile synthon (V), identical with the sample prepared by a known procedure.
- Thakur, S. B.,Jadhav, K. S.,Bhattacharyya, S. C.
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p. 675 - 683
(2007/10/02)
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- EINFACHE, REGIOSPECIFISCHE SYNTHESE VON CYCLOALKENONEN AUS LACTONEN
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The reaction of lithiumalkylphosphonates with γ- or δ-lactones followed by oxidation leads to 2,5- or 2,6-dioxophosphonates, which can be cyclized to cyclopentanones or cyclohexanones, respectively, constituting an easy, regiospecific route to cycloalkanones from lactones.
- Altenbach, Hans-Josef,Holzapfel, Winfried,Smerat, Gerd,Finkler, Stefan H.
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p. 6329 - 6332
(2007/10/02)
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- SYNTHESIS OF 2-(6'-CARBOXYHEXYL)CYCLOPENT-2-EN-1-ONE (PROSTAGLANDIN SYNTHON) BY CYCLIZATION OF 5-HYDROXYDODECANE-1,12-DIOIC ACID
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The oxidation of 2-(6'-carboxyhexyl)cyclopentanone by persulfuric acid leads to a mixture of 5-hydroxydodecane-1,12-dioic acid and the corresponding δ-lactone.Cyclodehydration of the latter with polyphosphoric acid gives 2-(6'-carboxyhexyl)cyclopent-2-en-1-one (prostaglandin synthon) with an overall yield of 41percent.
- Bobrova, N. I.,Pivnitskii, K. K.
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p. 259 - 261
(2007/10/02)
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- Prostaglandins Part 7. Synthesis of (+/-)-11-Deoxy-10-hydroxy- and (+/-)-11-Deoxy-10-oxoprostaglandins
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The epoxides of 2-alkylcyclopent-2-enones (I) react with acetic acid to give 5-acetoxy-2-alkylcyclopent-2-enones (II) which afford (+/-)-11-deoxy-10-hydroxyprostaglandins via conjugate-addition reactions.The 11-deoxy-10-hydroxyprostaglandin (IXa) readily undergoes base-catalysed autoxidation to the 11-deoxy-10-oxoprostaglandin (XIII).
- Caton, Michael P. L.,Darnbrough, Geoffrey,Parker, Trevor,Peart, Barry J.,Podmore, Michael L.,Threlfall, Terence L.
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p. 319 - 324
(2007/10/02)
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- Synthesis of Prostanoid Synthon and an Analogue
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2-(ω-Carboxyhexyl)cyclopent-2-en-1-one (VI), a prostanoid synthon and 2-(ω-carboxypentyl)cyclopent-2-en-1-one (IX) have been synthesized from aleuritic acid.
- Mukherjee, S. N.,Majee, R. N.
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p. 749 - 750
(2007/10/02)
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- Cyclopentane derivatives and their pharmaceutical compositions
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Cyclopentane derivatives of the formula: STR1 wherein R1 represents hydrogen or a carboxylic acyl group, R2 represents hydrogen or alkyl of 1 through 12 carbon atoms, and n represents an integer from 4 through 8, are new compounds possessing pharmacological properties, more particularly the production of hypertension and inhibition of gastric acid secretion. They are also useful in the preparation of 10-hydroxyprostaglandins.
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- Hydro substituted prostanoic acids and esters
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This disclosure describes certain 11-hydroxy and 11-deoxy-9-keto (or hydroxy)prostanoic acid derivatives useful as bronchodilators, anti-ulcer agents, or as intermediates.
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- Novel 11-hydroxy-9-keto-5,6-cis-13,14-cis-prostadienoic acid derivatives
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This disclosure describes certain 11-hydroxy and 11-deoxy-9-keto(or hydroxy)-prostanoic acid derivatives useful as bronchodilators, hypotensive agents, anti-ulcer agents, or as intermediates.
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- 1-Alkoximino-2-(ω-substituted alkyl)-2-cyclopentenes
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This disclosure describes certain 1-alkoximino-2-(ω-substituted-alkyl)-2-cyclopentenes useful as intermediates for the preparation of homologues, analogues, congeners, and derivatives of 9-oxo-13-trans-prostenoic acid and of 9-hydroxy-13-trans-prostenoic acid which have antimicrobial activity and prostaglandin-like hypotensive activity.
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- Derivatives of 9-hydroxy-13-trans-prostenoic acid
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This disclosure describes certain 15-deoxy prostanoic acid derivatives having a hydroxy group further along in the beta-chain, useful as bronchodilators, hypotensive agents, anti-ulcer agents, or as intermediates.
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- 3-Alkyl-2-(6-carboxyhexyl)cyclopentanones and esters and salts thereof
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This disclosure describes compounds of the class of substituted 9-oxoprostanoic acids and the esters and cationic salts thereof, useful as antimicrobial agents, hypotensive agents, anti-ulcer agents, or as intermediates, and novel processes for preparing the same.
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- Hydroxylated 15-deoxy derivatives of 9-hydroxy-13-trans-prostenoic acid
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This disclosure describes certain 15-deoxy prostanoic acid derivatives having a hydroxy group further along in the beta-chain, useful as bronchodilators, hypotensive agents, anti-ulcer agents, or as intermediates.
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- 2-Substituted-3,4-epoxycyclopentan-1-ones, and 2-substituted-3,4-epoxycyclopentan-1-ols
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This disclosure describes 2-substituted-3,4-epoxy-cyclopentan-1-ones, 2-substituted-3,4-epoxycyclopentan-1-ols, and various 2-substituted-cyclopentenones useful as intermediates for the preparation of certain 11-hydroxy- and 11-deoxy-9-keto(or hydroxy)-prostanoic acid derivatives which possess bronchodilator, hypotensive, and anti-ulcer activity.
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- 11-Deoxy-13-dihydro-prostaglandin-9-ketals
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This disclosure describes novel 11-deoxy-13,14-dihydro-prostaglandin-9-ketals useful as bronchodilators and as gastric acid secretion inhibitors.
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- Novel 15-substituted prostanoic acids and esters
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This disclosure describes compounds of the class of 15-substituted-9-keto(or 9-hydroxy)prostanoic acids and the esters and cationic salts thereof, useful as inhibitors of gastric acid secretion.
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- Lithium 3-triphenylmethoxy-1-trans-alkenyl-dialkyl alanates
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This disclosure describes 3-triphenylmethoxy-1-alkynes, 3-triphenylmethoxy-1-trans-alkenyl-dialkyl-alanes, and lithium 3-triphenylmethoxy-1-trans-alkenyl-dialkyl alanates useful as intermediates for the preparation of certain 11-hydroxy- and 11-deoxy-9-keto(or hydroxy)-prostanoic acid derivatives which possess bronchodilator, hypotensive, and anti-ulcer activity.
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