A six-step synthetic approach to marine natural product (+)-aureol. Issue 10 (7th March 2018) - Wang, Jun-Li
Graphical abstract: Highlights: Highly regioselective and stereoselective skeletal rearrangement reaction. Readily available and inexpensive starting material. Step-economical synthetic approach to the marine natural product (+)-aureol. Abstract: A concise synthetic approach to the marine natural product (+)-aureol has been achieved from readily available starting materials using obviously fewer steps in comparison to the related report in literature (6 steps versus 12 steps from (+)-sclareolide). Key steps of this protocol include a boron trifluoride-catalyzed domino 1, 2-H and 1, 2-methyl shifts and a nickel(II)-catalyzed cross-coupling reaction between an alkyl iodide and an aryl Grignard reagent.