Selective Synthesis of Deuterated cis- and trans-Isohumulones and trans-Isohumulinones
Bruce C. Hamper,
Hunter J. Campbell,
Rensheng Luo
et al.
Abstract:Deuterated isohumulones can be prepared directly from humulones by an acyloin ring contraction under either magnesium catalyzed basic conditions or photochemical induced reaction in deuterated solvents. Reaction of humulones with biphasic methylene chloride/aqueous NaOD and MgSO4 in D2O gave stereoselective formation of cis-3d- isohumulones (cis-trans ratio of 82:18) as the magnesium salts in 71-83% yield. Greater than 95% incorporation of three deuterons was observed in the C5 position of the pentenone ring… Show more
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