PROCESS FOR THE MANUFACTURE OF PROSTAGLANDINS AND PROSTAGLANDIN-LIKE COMPOUNDS

摘要

1334952 Cyclopentane derivatives IMPERIAL CHEMICAL INDUSTRIES Ltd 2 Dec 1971 [6 Jan 1971] 662/71 Heading C2C The invention comprises a process for the manufacture of prostaglandins of the formula wherein R1 is OH and R2 is H or R1 and R2 together form O, R3 is a hydrocarbon chain optionally bearing one or more substituents and containing a COOH, alkoxycarbonyl or CH 2 OH, and R4 is a group of predominantly hydrocarbon character, which includes the oxidative cleavage of bicyclo[2,2,1]heptane derivatives of the formula wherein R5 and R6 each are C 1-6 alkyl or C 7-20 aralkyl and the novel cyclopentane derivatives of the formula obtained by the said oxidative cleavage. Intermediates and startinq materials also prepared are:- 5-endo-benzyloxymethyl-6-exohydroxymethylbicyclo[2,2,1]-hept-2-ene, 5- endo - benzyloxymethyl - 6 - exo - methoxymethylbicyclo[2,2,1]hept-2-ene, 6-exo-dimethoxy-5-endo-hydroxymethylbicyclo[2,2,1]hept-2- ene, 5-endo-benzyloxymethyl-6-exo-dimethoxymethylbicyclo[2,2,1]hept-2-ene, 6-exo-dimethoxymethylbicyclo[2,2,1]-hept-2-ene-5-endo carboxaldehyde, 2α-benzyloxymethyl-1α,4α,bis- (1 - hydroxyethyl) - 3# - methoxymethylcyclopentane, 1α,4α-diacetyl-2α-benzyloxy-methyl - 3#-methoxymethylcyclopentane, 5-endo-6-exobis benzyloxymethylbicyclo[2,2,1]hept-2-ene, 1α,4α-diacetyl-2α,3#-bisbenzyloxymethylcyclopentane, 1α,4α-diacetoxy-2α-benzyloxymethyl- 3#-methoxymethylcyclopentane, 1α,4α-diacetoxy-2α - hydroxymethyl - 3# - methoxymethylcyclopentane and the p-toluenesulphonate ester thereof, 1α,4α-diacetoxy-2α-cyanomethyl-3#- methoxymethylcyclopentane, 2α-cyanomethyl- 1α,4α - dihydroxy - 3# - methoxymethylcyclopentane, the lactone of 2α-carboxymethyl-3#- methoxymethylcyclopentane-1α,4α-diol, the lactone of 4α-acetoxy-2α-carboxymethyl-1α- hydroxy-3#-methoxymethylcyclopentane, 1α,4α diacetoxy - 2α,3# - bisbenzyloxymethylcyclopentane, 1α,4α-diacetoxy-2α,3#-bishydroxymethylcyclopentane, 4α-acetoxy-2α-acetoxymethyl - 3# - hydroxymethyl - 1α - cyclopentanol, 1α,4α-diacetoxy-2α,3#-bis(triphenylmethoxymethyl)cyclopentane, 4α - acetoxy - 2α-acetoxymethyl-3#-triphenylmethoxymethyl-1α-cyclopentanol, 2α - hydroxymethyl - 3# - triphenylmethoxymethylcyclopentane-1α,4α-diol, 2α- (p - toluenesulphonylmethyl) - 3# - triphenylmethoxymethylcyclopentane - 1α,4α-diol, and the 1α,4α-diacetate thereof, 1α,4α-diacetoxy-2α- cyanomethyl - 3# - triphenylmethoxymethylcyclopentane, 1α,4α-diacetoxy-2α-cyanomethyl- 3#-hydroxymethylcyclopentane and the lactone of 2α-carboxymethyl-3#-hydroxymethylcyclopentane-1α,4α-diol.