Abstract
Reduction of methyl 8-ethoxy-6-oxoöctanoate (IX) to its 6-hydroxy compound (X) was effected in better yield by high-pressure reduction over Raney nickel than with sodium borohydride. The 6-hydroxy compound was acylated to form (XI) and (XII), while its hydrolysis gave the acid (XVII). Heating of the acid (XVII) resulted in formation of a small amount of the lactone (XVIII).
Reduction of methyl 8-acetoxy-6-oxoöctanoate (XXVII) also afforded the 6-hydroxy compound (XXVIII) in better yield by high-pressure reduction over Raney nickel. (XXVIII) was hydrolyzed to 6, 8-dihydroxyoctanoic acid (XXV) and this was esterified to (XXIV). Acetylation of the dihydroxy compound (XXIV) or 6-hydroxy compound (XXVIII) afforded methyl 6, 8-diacetoxyoctanoate (XXII: R=CH3).
High-pressure reduction of methyl 8-benzyloxy-6-oxoöctanoate (XXIX) resulted in formation of 6-hydroxy (XXX) or 6, 8-dihyclroxy compound (XXIV) according to reduction conditions.
