A SHORT SYNTHESIS OF POTENTIAL JUVENOIDS BASED ON THE ISOXAZOLE CHEMISTRY

3,4,5-Trisubstituted isoxazoles (1) and (4) afforded, after chromic ox idation and borohydride reduction, (3-methyl-5-phenylisoxazol-4-yl)-6- hydroxyhexanoic acid (2) or soxazol-4-yl)-3,4-dihydro-1H-2-benzopyran- 3-ona(5) which were reduced to (+/-)-(Z/E)-3-methyl-7-benzoyl-8-oxonon -6-enoic acid (3) and (E)-2-(2-[2-benzoyl-3-oxobut-1-enyl]-phenyl)acet ic acid (6) with molybdenum hexacarbonyl. Lactone (5) afforded a singl e E-diastereoisomer of acid (6). Catalytic hydrogenation of 5 afforded selectively isoxazole (7) which was reduced with molybdenum hexacarbo nyl to 2-(2-[2-benzoyl-3-oxobutyl]phenyl)acetic acid (8). Structures o f products are related with those of some juvenoids.