1358469 Derivatives of desmethyl retenoic acid UNIVERSITY OF CALIFORNIA REGENTS OF 12 Dec 1972 [13 Dec 1971] 57332/72 Headings C2C and C2V 2,6,6 - trimethyl - 1 - (10SP1/SP- carboxydeca 1SP1/SP,3SP1/SP,- 5SP1/SP,7SP1/SP,9SP1/SP-pentaeryl)cyclohex-1-ene is prepared by (a) subjecting #-ionone to a haloform reaction (preferably chloroform) to form 2,6,6-trimethyl- 1-(2SP1/SP-carboxyvinylene)-cyclohexa-1-ene, (b) reducing the acid to the corresponding alcohol (preferably using lithium aluminium hydride in diethyl (ether), (c) oxidizing the alcohol to the corresponding aldehyde (preferably using manganese dioxide), (d) subjecting the aldehyde to a Wittig reaction (preferably in the presence of sodium hydride) using a compound (R 1 O)(R 2 O)- P(O)CH 2 -CH=CH-COOR 3 in which R 1 ,R 2 and R 3 are alkyl or aryl (preferably ethyl) (e) hydrolysing the ester formed to the corresponding acid and repeating the reaction sequence (b) to (e). A modification of this process repeats steps (a) to (c) and subjects the aldehyde to a Wittig reaction using (R 1 O))(R 2 O)P(O)CH 2 - (CH=CH) 3 -COOR 3 and to produce the ester of the decapentaenoic acid directly. 2,6,6-Trimethyl - 1 - (12SP1/SP - carboxydodeca - 1SP1/SP,3SP1/SP,5SP1/SP,7SP1/SP,9SP1/SP,11SP1/SP- hexaenyl)cyclohex-1-ene is prepared from the decapentaenoic acid by repeating steps (b) and (c) and reacting the resulting aldehyde with (R 1 O) (R 2 O)P(O)CH 2 COOR 3 and hydrolysing the resulting ester. The above acids are active in promoting wound-healing and form with a carrier or diluent a pharmaceutical composition which may be administered topically.
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