Total Synthesis of (−)-Dimatairesinol via Regioselective Intermolecular Oxidative Phenol Coupling
1
Issued Date
2025-01-01
Resource Type
ISSN
15237060
eISSN
15237052
Scopus ID
2-s2.0-105010204264
Journal Title
Organic Letters
Rights Holder(s)
SCOPUS
Bibliographic Citation
Organic Letters (2025)
Suggested Citation
Chatpreecha R., Leowanawat P., Kuhakarn C., Reutrakul V., Soorukram D. Total Synthesis of (−)-Dimatairesinol via Regioselective Intermolecular Oxidative Phenol Coupling. Organic Letters (2025). doi:10.1021/acs.orglett.5c01942 Retrieved from: https://repository.li.mahidol.ac.th/handle/123456789/111228
Title
Total Synthesis of (−)-Dimatairesinol via Regioselective Intermolecular Oxidative Phenol Coupling
Author's Affiliation
Corresponding Author(s)
Other Contributor(s)
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.