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Dihydroxerulin (5) is a noncytotoxic inhibitor of cholesterol biosynthesis. In spite of being achiral and devoid of OH groups, it was synthesized efficiently in 2×5 steps in two linear sequences plus one terminating step, from the optically active, multiply hydroxylated L-gulonolactone via the key intermediates 1–4. 1H NMR spectroscopy revealed that the C8=C9 bond of synthetic and natural 5 is trans-substituted.
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Siegel et al. (1998) studied this question.
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