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Starting from 2-methylfuran and crotonaldehyde, both jungianol and epi-jungianol were prepared by a six-step sequence including a gold-catalyzed arene synthesis and a photochemical S(N)2-like reduction with lithium aluminum hydride. Not a single protective group was needed in the entire synthesis. With both diastereomers in hand, the stereochemical assignment in the literature could be corrected by means of a thorough (1)H NMR spectroscopic analysis and an X-ray diffraction study on an epi-jungianol derivative.
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Hashmi et al. (2003) studied this question.
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