Abstract
The hydroxymercuration (OM) reaction of nonconjugated diene system of aucubin (1) with at least 2 equivalents of Hg(II) salts involved not only the enol ether Δ 3 double bond, but also the less reactive Δ 7 cyclopentene double bond; the unique intermediate was observed to be the organobismercurial derivative (10). Surprisingly, the reductive demercuration (DM) of 10 with NaBH 4 gave a mixture of three products isoeucommiol (3), 6-hydroxy-8,9-dihydroxymethyl-2-oxabicyclo[3.2.1]oct-3-ene (5), and 7,8-dihydro-8-α-hydroxyisoeucommiol (6). The way these different compounds may be formed from common intermediate (10) is discussed
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