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filingDate 1973-09-17-04:00^^<http://www.w3.org/2001/XMLSchema#date>
publicationDate 1976-03-03-04:00^^<http://www.w3.org/2001/XMLSchema#date>
publicationNumber GB-1426773-A
titleOfInvention Cyclopentane derivatives
abstract 1426773 Cyclopentane derivatives MERCK & CO Inc 17 Sept 1973 [20 Sept 1972] 43532/73 Heading C2C The invention comprises the alkyl or aralkyl esters of (8#-acetyl-7α-carboxy-1,4-dioxaspiro- [4,4]non - 6# - yl)heptanoic acid, the alkyl or aralkyl esters of (8#-acetoxy-7α-carboxy-1,4- dioxaspiro[4,4]non - 6# - yl)heptanoic acid, the alkyl and aralkyl esters of (8#-acetoxy-7α- halocarbonyl - 1,4 - dioxaspiro[4,4]non - 6# - yl)- heptanoic acid, and the alkyl and aralkyl esters of (8# - acetoxy - 7α - (1 - midazalylcarbonyl)- 1,4 - dioxaspiro[4,4]non - 6# - yl]heptanoic acid, their preparation and the conversion of the last two named compounds into the corresponding alkyl or aralkyl esters of (8#- acetoxy - 7α - formyl - 1,4 - dioxaspiro[4,4] non - 6# - yl)heptanoic acid by treating them with reducing agents. The following intermediates are also prepared:- 6 - (6 - carboxymethoxycarbonylhexyl) - 8 - (1,1 - dihydroxyethyl) - 1,4 - dioxaspiro[4,4]nonane - 7 - carboxylic acid γ - lactone, 6 - [6 - (1,3 - dioxolan - 2 - yl) hexyl] - 8 - (1 - hydroxyethyl) - 1,4-dioxaspiro- [4,4]nonane - 7 - carboxylic acid γ - lactone, 6 - (6 - formylhexyl) - 8 - (1 - hydroxyethyl)- 1,4 - dioxaspiro[4,4]nonane - 7 - carboxylic acid γ - lactone, 8 - (1 - hydroxyethyl) - 6 - [6- (1 - imidazolylcarbonyl)hexyl] - 1,4 - dioxaspiro- [4,4]nonane - 7 - carboxylic acid γ - lactone, 6 - (6 - carbonylhexyl) - 8 - (1 - hydroxyethyl- 1,4 - dioxaspiro[4,4]nonane - 7 - carboxylic acid γ - lactone, 6 - (6 - methoxycarbonylhexyl) - 8 - (1 - hydroxyethyl) - 1,4-dioxaspiro- [4,4]nonane - 7 - carboxylic acid γ - lactone, 5 - (1 - hydroxyethyl) - 2 - (6 - methoxycarbonylhexyl) - 3 - oxocyclopentanecarboxylic acid γ - lactone, 4 - carboxymethyl - 3 - (1 - carboxy- 7 - methoxycarbonylheptyl)- 5 - methyltetrahydrofuran - 2 - one, 6 - (1 - hydroxyethyl)- 2 - (6 - methoxycarbonylhexyl) - 3 - cyolohexene - I - carboxylic acid γ - lactone, and methyl 8,10-undecadienoate. The following process is also exemplified:- methyl (8# - acetoxy - 7α - formyl - 1,4 - dioxaspiro[4,4]non - 6# - yl)heptanoate#methyl [8# - acetoxy - 7α - (3 - oxo - trans - 1 - octenyl)- 1,4 - dioxaspiro[4,4]non - 6# - yl]heptanoate# methyl [8# - acetoxy - 7α - (3 - hydroxy - trans- 1 - octenyl) - 1,4 - dioxaspiro[4,4]non - 6# - yl] heptanoate#methyl [8# - hydroxy - 7α - (3- hydroxy - trans - 1 - octenyl) - 1,4 - dioxaspiro- [4,4]non-6#-yl]heptanoate and racemic PGE 1 .
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