| Abstract: | The first syntheses of syn-12-hydroxydieldrin, syn-12-hydroxyendrin and anti-12-hydroxyendrin have been accomplished by debenzoylation and epoxidation of three isomeric adduction products of hexachlorocyclopentadiene and 1,7,7-trinorborna-2,5-dien-7-yl benzoate. A third known metabolite of endrin, 12-ketoendrin, and a putative metabolite of dieldrin, 12-ketodieldrin, were prepared from the corresponding alcohols by oxidation with chromium trioxide. Characterisation of the three debenzoylated intermediates as syn-12-hydroxyaldrin, and syn- and anti-12-hydroxyisodrin constitutes the first syntheses of these three possible metabolites of aldrin and isodrin. |
