A six-step synthetic approach to marine natural product (+)-aureol. Issue 10 (7th March 2018)

• Record Type: Journal Article
• Authors: Wang, Jun-Li; Li, Hui-Jing; Wang, Meirong; Wang, Jun-Hu; Wu, Yan-Chao
• Is Part Of: Tetrahedron letters. Volume 59:Issue 10(2018)
• Page Start: 945
• Page End: 948
• Publication Date: 2018-03-07
• Subjects: Aureol -- Rearrangement -- Coupling reaction -- Marine natural products; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2018.01.091
• Languages: English
• ISSNs: 0040-4039

Abstract

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.