Total Asymmetric Synthesis and Stereochemical Confirmation of (+)- and (−)-Lyoniresinol and Its Deuterated Analogues

• Published in: Journal of organic chemistry Vol. 87; no. 6; pp. 4254 - 4262
• Main Authors: Luong, Tuan Minh, Pilkington, Lisa I, Barker, David
• Format: Journal Article
• Language: English
• Published: United States American Chemical Society 18.03.2022
• Subjects: Anisoles - analysis; Naphthalenes; Taste; Wine - analysis
• ISSN: 0022-3263; 1520-6904
• DOI: 10.1021/acs.joc.1c03085

Lyoniresinol and its derivatives are lignans which have been isolated from a plethora of plant species. In addition to exhibiting a range of interesting biological activities including anticancer, anti-inflammatory, antimicrobial, and others, these compounds have also been discovered in wines and spirits and shown to have gustatory effects in these alcoholic matrices. (+)-Lyoniresinol 1 is reported to impart a strong bitter taste while its enantiomer (−)-lyoniresnol 2 is tasteless. The first total asymmetric synthesis of both natural enantiomers (+)-1 and (−)-2 and their deuterated analogues (D 4)-(+)-3 and (D 4)-(−)-4 has been achieved, confirming the structure and stereochemistry of the natural products. The synthesized compounds can be utilized as internal standards in stable isotope dilution analysis for improving and optimizing the existing lyoniresinol quantitation methods in the future.