Asymmetric total synthesis of four bioactive lignans using donor-acceptor cyclopropanes and bioassay of (-)- and (+)-niranthin against hepatitis B and influenza viruses

Ryotaro Ota; Daichi Karasawa; Mizuki Oshima; Koichi Watashi; Noriko Shimasaki; Yoshinori Nishii

doi:10.1039/d2ra00499b

Asymmetric total synthesis of four bioactive lignans using donor-acceptor cyclopropanes and bioassay of (-)- and (+)-niranthin against hepatitis B and influenza viruses

RSC Adv. 2022 Feb 7;12(8):4635-4639. doi: 10.1039/d2ra00499b. eCollection 2022 Feb 3.

Authors

Ryotaro Ota¹, Daichi Karasawa¹, Mizuki Oshima^{2

3}, Koichi Watashi^{2

3

4}, Noriko Shimasaki⁵, Yoshinori Nishii¹

Affiliations

¹ Department of Chemistry and Materials, Faculty of Textile Science and Technology, Shinshu University Tokida 3-15-1, Uea Nagano 386-8567 Japan nishii@shinshu-u.ac.jp.
² Department of Virology II, National Institute of Infectious Diseases Toyama 1-23-1 Shinjuku-ku Tokyo 162-8640 Japan.
³ Department of Applied Biological Sciences, Tokyo University of Science Yamazaki 2641 Noda-shi Chiba 278-8510 Japan.
⁴ Research Center for Drug and Vaccine Development, National Institute of Infectious Diseases Toyama 1-23-1 Shinjuku-ku Tokyo 162-8640 Japan.
⁵ Department of Virology III, National Institution of Infections Deseases Gakuen 4-7-1 Musashimurayama-shi Tokyo 208-0011 Japan.

Abstract

The asymmetric total synthesis of four lignans, dimethylmatairesinol, matairesinol, (-)-niranthin, and (+)-niranthin has been achieved using reductive ring-opening of cyclopropanes. Moreover, we performed bioassays of the synthesized (+)- and (-)-niranthins using hepatitis B and influenza viruses, which revealed the relationship between the enantiomeric structure and the anti-viral activity of niranthin.