Work

Total synthesis of quasi-symmetric dihydrofuran lignans (−)-ribesin A and B isolated from Ribes nigrum leaves

Year: 2025

Type: article

Abstract: Dihydrofuran lignans ribesin A ( 1 ) and ribesin B ( 2 ) isolated from Ribes nigrum leaves were chemically synthesized for the first time using oxa-Michael addition–carbocyclization and double-bond migration as key steps. However, the NMR data of synthesized ribesin B ( 2 ) with vanillin scaffolds were slightly inconsistent with those of reported ribesin B ( 2 ). Through further synthetic study, the structure of natural ribesin B ( 2 ) was revised to that of 3 , which has unique isovanillin scaffolds. Moreover, the asymmetric total synthesis of natural products ribesin A ( 1 ) and ribesin B ( 3 ) was achieved using chiral propargyl alcohols as the starting materials prepared via lipase-catalyzed kinetic resolution. • Dihydrofuran lignans ribesin A and B were chemically synthesized. • The structure of ribesin B was revised to an isovanillin derivative. • The asymmetric synthesis of natural (−)-ribesin A and B was achieved.

Source: Tetrahedron

DOI: 10.1016/j.tet.2025.134675

Authors: Kae Horio, Hayato Maeda, Kayo Horie, Naoki Nanashima, Ken-ichi Nihei

Institutions: Tokyo University of Agriculture and Technology, Hirosaki University, Aomori University of Health and Welfare, Utsunomiya University

Language: English

Topic: Plant-derived Lignans Synthesis and Bioactivity

Subfield: Molecular Biology

Field: Biochemistry, Genetics and Molecular Biology

Domain: Life Sciences

Open Access status: hybrid

Estimated APC paid: $3,680

Funder: Japan Society for the Promotion of Science