Gold catalysis:: Efficient synthesis and structural assignment of jungianol and epi-jungianol

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 H-1 NMR spectroscopic analysis and an X-ray diffraction study on an epi-jungianol derivative.