Related Experiment Video
Updated: Sep 16, 2025

Retropinacol/Cross-pinacol Coupling Reactions - A Catalytic Access to 1,2-Unsymmetrical Diols
Published on: April 4, 2014
Total Synthesis of (-)-Dimatairesinol via Regioselective Intermolecular Oxidative Phenol Coupling
Rungrawin Chatpreecha1, Pawaret Leowanawat1,2, Chutima Kuhakarn1,2
1Department of Chemistry, Faculty of Science, Mahidol University, Rama VI Road, Bangkok 10400, Thailand.
Abstract:
We report the total synthesis of (-)-dimatairesinol, a new dimeric natural lignan possessing a unique interconvertible biaryl skeleton coupled at C-5/C-5 of two units of dibenzyl γ-butyrolactone lignan, namely, matairesinol. The key step involved high regioselective formation of a C-5/C-5 biaryl bond between two units of chiral phenolic γ-butyrolactone (R = H) via a direct and metal-free oxidative phenol coupling mediated by PIFA. On the contrary, C-6/C-6 biaryl coupling exclusively took place when nonphenolic γ-butyrolactones (R ≠ H) were employed, providing the corresponding biaryl products as atropisomers. Synthetic manipulations on the C-5/C-5-biaryl intermediate led to (-)-dimatairesinol.
More Related Videos
07:36Versatile CO2 Transformations into Complex Products: A One-pot Two-step Strategy
Published on: November 9, 2019
06:34Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides CHIPS
Published on: June 20, 2014
Related Concept Videos
Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide
Vicinal Diols via Reductive Coupling of Aldehydes or Ketones: Pinacol Coupling Overview
Oxidation of Alkenes: Anti Dihydroxylation with Peroxy Acids
Preparation of Diols and Pinacol Rearrangement
The reaction begins with transferring a proton from the acid catalyst to one of the hydroxyl groups, producing an oxonium ion.
[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction
Diels–Alder Reaction Forming Cyclic Products: Stereochemistry