Abstract
An efficient synthesis of the title compound (5) from Thiele's ester (1b) is described. Thus, LiAlH4 promoted reduction of dimethyl pentacyclo[5.4.0.02,5.03,904,8]decane-2,5-dicarboxylate (2) produced the corresponding diol, 3, in 80% yield. Reaction of 3 with NaH-MsCl followed by LiAlH4 promoted reduction of the crude product thereby obtained resulted in the formation of the title compound (5, 12% yield) accompanied by a cage-annulated oxa[3.3.2]propellane, 6, which proved to be the major reaction product (22% yield). Reaction of 3 with Et3N-MsCl afforded the corresponding dimesylate, 4, in essentially quantitative yield). Subsequent LiAlH4 promoted reduction of 4 gave 5 in 66% yield.
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