Prostaglandin intermediates

Details Prostaglandin intermediates Prostaglandin intermediates

C - Chemistry, Metallurgy

07

C

260/235.01, 260/

C07C 59/74 (2006.01) C07C 59/80 (2006.01) C07D 493/08 (2006.01)

Patent

CA 1198421

ABSTRACT PROSTAGLANDIN INTERMEDIATES A process for the preparation of a compound of formula (I) Image (I) wherein Image represents one of the divalent cyclic groups Image Image the letters a and b indicating in each case the points of attachment of the substituents R1 and Image respectively; R1 represents a 6-carboxyhex-2-enyl group or a modification thereof in which the group is altered by one, or where appropriate by a combination, of the following: (a) reduction of the double bond optionally accom- panied by replacement of a carbon atom at the 1, 2 or 3 position by a sulphur or oxygen atom, (b) alteration of the position of the double bond, (c) shortening or lengthening of the carbon chain by one or two methylene groups, and (d) formation of an amide, ester or salt derivative of the carboxy group; R2 represents hydrogen, a C1-10 aliphatic hydrocarbon group or a C1-10 aliphatic hydrocarbon group substituted directly or through an oxygen or sulphur atom by an aromatic group Ar, where Ar is a phenyl, napthyl. fluorenyl, dibenzo- cyclohexyl, dibenzocycloheptyl, pyridyl, benzothiazolyl, dihydrobenzothiazolyl, N-methyldihydroenzothinzolyl, benzoxazolyl, dihydrobenzoxazolyl or N-methyldihydrobenzoxazolyl group or such a group substituted by one or more substituents selected from C1-10 alkoxy, halogen, C1-10 halogen substituted alkyl, sulphamoyl, amino, hydroxyl, nitro and C1-10 alkyl groups; and either V and W together represent the oxygen atom of a carbonyl group or, when R2 is other than hydrogen, V represents hydrogen and W represents a hydroxy group; with the proviso that when R2 is hydrogen then the divalent cyclic group is a bicyclo [2,2,2] octane, a bicyclo [2,2,2] oct-2Z-ene or a 6,6-dimethyl-bicyclo [3,1,1] heptane ring system comprises reacting a compound of formula (II) Image (II) in which Z represents (a) a formyl group in acetal form, (b) a hydroxy- methyl group, (c) a formyl group or (d) a group CH(R2)OH, Y is either R1 as defined for (I) or a precursor for R1 and X and R2 are as defined for (I), the said reaction consisting of (a) effecting hydrolysis of the acetal to give a formyl group, (b) effecting oxidation of the hydroxymethyl group to give a formyl group, (c) effecting a Grignard reaction involving the formyl group and a reagent R2MgHalogen to give a group CH(R2OH), or (d) effecting oxidation of the group CH(R2OH) to give a group C(R2)=O, and where appropriate converting the group Y in the resultant product into a group R1, the process optionally involving a change of stereochemistry of (I) to that of (II). The compounds prepared by this process are of value for the production of biologically active prostaglandin compounds.

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