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The configurations of 4βH-thujan-2-one (isodihydroumbellulone) and the two 4βH-thujan-2-ols (neoiso- and iso-dihydroumbellulols) have been determined by 1H and 13C n.m.r. spectroscopy. Based on these data, the reduction of the title compounds by metal hydrides and alkoxides has been shown to be consistent with control of stereoselectivity by the reactant conformation.
C. M. Holden, J. C. Rees, S. P. Scott and D. Whittaker, J. Chem. Soc., Perkin Trans. 2, 1976, 1342 DOI: 10.1039/P29760001342
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