Dimerization of Allylbenzenes into Cyclolignans by a Metathesis-Oxidation Sequence
Abstract
Allylbenzenes form dimeric cyclolignans in a two-step, one-pot sequence involving Ru-catalyzed olefin metathesis followed by iron- or acid-catalyzed oxidation with DDQ. Alternatively, performing the oxidation step under wet conditions leads to benzyl styryl ketones as the major products. The mechanistic investigation suggests that the oxidation process relies on the combination of single electron transfer, hydrogen atom transfer, and proton transfer steps. The developed metathesis-oxidation sequence enables a straightforward and scalable preparation of arylnaphthalene and aryltetralin types of cyclolignans, such as oleralignan B and its derivatives.
Fields of Study & Subjects
Plant-derived Lignans Synthesis and Bioactivity
Synthetic Organic Chemistry Methods
Magnolia and Illicium research
Publication details
- Journal / source
- The Journal of Organic Chemistry
- Publisher
- American Chemical Society (ACS)
- Volume
- 91
- Issue
- 10
- Pages
- 3669–3676
- Publication date
- 26 February 2026
- Language
- EN