Regio- and stereo-specific reduction of the exo-epoxy alcohol 5 with LiAID4 produced the 4α-D-trans-3,5-diol 7 and the 4β-D-trans-3,5-diol 8 in varying ratios, an indication that in spite of epoxide rearrangement between 5 and 6 direct epoxide ring-opening of 5 to afford the 3,5-diol 4 is the primary pathway.
Z. Liu and X. Chu, J. Chem. Soc., Perkin Trans. 1, 1993, 2155 DOI: 10.1039/P19930002155
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