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 (1)H NMR spectroscopic analysis and an X-ray diffraction study on an epi-jungianol derivative.
D002384:Catalysis; D018360:Crystallography, X-Ray; D006046:Gold / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D008956:Models, Chemical; D015394:Molecular Structure; D010084:Oxidation-Reduction; D010636:Phenols / Q000138:chemical synthesis* / Q000737:chemistry; D012717:Sesquiterpenes / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D010636:Phenols; D012717:Sesquiterpenes; C481868:jungianol; D006046:Gold