Abstract
Diethyl 3, 6-dioxooctanedioate (5), which can be prepared readily from ethyl acetoacetate and ethyl γ-bromoacetoacetate, was utilized for a facile preparation of dl-dehydroiridodiol (1). Compound 5 was treated with sodium hydroxide to give ethyl 2-ethoxycarbonyl-3-oxo-1-cyclopenteneacetate (6), which was methylated, and then reduced to give ethyl 2-(2-ethoxycarbonyl-3-oxocyclopentyl) propionate (8). Compound 8 was transformed to the phosphate (9). On methylation with lithium dimethylcuprate, followed by reduction, the phosphate (9) was converted to dl-dehydroiridodiol (1) via ethyl 2-(2-ethoxycarbonyl-3-methyl-2-cyclopentenyl) propionate (10).
