| abstract |
The invention comprises d, l and dl compounds of formula wherein R is C 1-6 alkyl R 1 is H, alkyl or dialkylaminoalkyl R 2 is carboxy, alkoxycarbonyl, dialkylaminoalkoxycarbonyl, hydroxymethyl, methoxymethyl or acyloxymethyl Z is optionally thioketalized CO, CHOH, CHOAcyl, CHOCH 3 , C(OH)C: CH or C: NOH Y is CH 2 , CO, C: NOH, C: CHOH, C: CHSR 3 or C: CHNR 4 R 5 (where R 3 is alkyl and R 4 and R 5 are each alkyl or aryl) and lactones of those compounds wherein R 2 is carboxy and Z is CHOH and acid-addition salts of those compounds having basic groups. These compounds are prepared by alkylating compounds of formula wherein X is a protecting group (e.g. benzylidene, furfurylidene, CHSR 3 or CHNR 4 R 5 ) to introduce the group R, converting the group CX in the resulting product to a group Y (when it is not already such a group) and, when required converting the 1-keto group to other groups Z. Many product interconversions are described and exemplified. dl - 5 - (N - methyl - anilinomethylene) - 3 - (6 - methoxy - 2 - naphthyl) - cyclopentanone - 2 - acetic acid and its methyl ester are prepared from dl-methyl 3 - (6 - methoxy - 2 - naphthyl) - cyclopentanone - 2 - acetate via dl - 5 - hydroxymethylene - 3 - (6 - methoxy - 2 - naphthyl) cyclopentanone - 2 - acetic acid. Said methyl ester is also obtainable from the parent acid. |