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Paper | Regular issue | Vol 36, No. 10, 1993, pp.2259-2265
Published online, 1st January, 1970
DOI: 10.3987/COM-92-6209
A Short Synthesis of Potential Juvenoids Based on the Isoxazole Chemistry

Lourdes Martin, Cecilia Polo, Vicente Ramos, Tomás Torroba,* and Stefano Marcaccini

*Departamento de Química Orgánica, Facultad de Veterinaria, Universidad de Extremadura, E-10071 Cáceres, Spain


3,4,5-Trisubstituted isoxazoles (1) and (4) afforded, after chromic oxidation and borohydride reduction, (±)-3-methyl-6-(3-methyl-5-phenylisoxazol-4-yl)-6-hydroxyhexanoic acid (2) or (±)-1-(3-methyl-5-phenylisoxazol-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)acetic acid (6) with molybdenum hexacarbonyl. Lactone (5) afforded a single E-diastereoisomer of acid (6). Catalytic hydrogenation of 5 afforded selectively isoxazole (7) which was reduced with molybdenum hexacarbonyl to 2-(2-[2-benzoyl-3-oxobutyl]phenyl)acetic acid (8). Structures of products are related with those of some juvenoids.