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

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

doi:10.1039/d2ra00499b

RSC Adv.

2022

DOI: 10.1039/d2ra00499b

|View full text |Cite

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

et al.

Abstract: The total synthesis of four lignans including (−)- and (+)-niranthin has been achieved utilizing cyclopropanes. Based on bioassays of the (+)- and (−)-niranthins using HBV and IFV, we speculated the bioactive site of niranthin against HBV and IFV.

Help me understand this report

Search citation statements

Order By: Relevance

Paper Sections

Select...

Citation Types

Supporting

Mentioning

Contrasting

Year Published

2022

2023

Publication Types

Select...

Article3

Relationship

Self Cite0

Independent3

Authors

Journals

Cited by 3 publications

References 45 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

Rapid and Safe Continuous‐Flow Simmons‐Smith Cyclopropanation using a Zn/Cu Couple Column

Nova‐Fernández,

Pascual‐Coca,

Cabrera

et al. 2023

Adv Synth Catal

View full text Add to dashboard Cite

Flow chemistry has recently opened new chemistry windows thanks to the safer use of hazardous and sensitive reagents. Furthermore, flow procedures usually outperform their batch counterparts due to improved mass and heat transfer, offering a good opportunity for industrial application. Herein, a rapid Simmons‐Smith cyclopropanation flow process is presented. Taking advantage of the in situ production of the zinc carbenoid species, several olefins bearing aromatic rings of different electronic nature, aliphatic chains or heterocycles were smoothly cyclopropanated with a residence time of just 15 minutes. In addition, industrial applicability of the protocol is assured thanks to a successful 12‐mmol scale experiment, which represents a 3.59 grams per hour production of a selected example, and to the satisfactory synthesis of pharmaceutical drugs.

show abstract

Rapid and Safe Continuous‐Flow Simmons‐Smith Cyclopropanation using a Zn/Cu Couple Column

Nova‐Fernández,

Pascual‐Coca,

Cabrera

et al. 2023

Adv Synth Catal

View full text Add to dashboard Cite

show abstract

Asymmetric Total Synthesis of a Bioactive Lignanamide Using a 5‐endo‐tet‐Type Cyclization of Activated Cyclopropylcarbinols and Synthetic Support for the Reaction Mechanism

et al. 2022

View full text Add to dashboard Cite

The first enantioselective total synthesis of a bioactive lignanamide was achieved with high enantiomeric excess. Key synthetic steps include an organocatalytic enantioselective cyclopropanation and a Lewis-acid-mediated chirality-transferring 5-endo-tet-type cyclization that proceeds with a very high degree of stereoinduction. The proposed mechanism of the key reaction is supported by the experimental results. Based on these experimental results, the 5-endo-tet-type cyclization of a cyclopropylcarbinol proceeds predominantly via an S N 1 mechanism with high trans-selectivity, which arises from the steric hindrance of the neighboring substituent. Minor pathways include the anchimeric participation of (i) the oxygen atom of the benzoyl group in an S N 2 mechanism and/or (ii) a benzenecoordinated transition state in an S N 1-like mechanism.

show abstract

Asymmetric Synthesis of Bioactive Lignans and Enantiomeric Antiviral Activity of Niranthin

2022

Synfacts

View full text Add to dashboard Cite

scite is a Brooklyn-based organization that helps researchers better discover and understand research articles through Smart Citations–citations that display the context of the citation and describe whether the article provides supporting or contrasting evidence. scite is used by students and researchers from around the world and is funded in part by the National Science Foundation and the National Institute on Drug Abuse of the National Institutes of Health.

Contact Info

hi@scite.ai

10624 S. Eastern Ave., Ste. A-614

Henderson, NV 89052, USA

Blog Terms and Conditions API Terms Privacy Policy Contact Cookie Preferences Do Not Sell or Share My Personal Information

Made with 💙 for researchers

Part of the Research Solutions Family.

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

Abstract: The total synthesis of four lignans including (−)- and (+)-niranthin has been achieved utilizing cyclopropanes. Based on bioassays of the (+)- and (−)-niranthins using HBV and IFV, we speculated the bioactive site of niranthin against HBV and IFV.

Cited by 3 publications

References 45 publications

Rapid and Safe Continuous‐Flow Simmons‐Smith Cyclopropanation using a Zn/Cu Couple Column

Rapid and Safe Continuous‐Flow Simmons‐Smith Cyclopropanation using a Zn/Cu Couple Column

Asymmetric Total Synthesis of a Bioactive Lignanamide Using a 5‐endo‐tet‐Type Cyclization of Activated Cyclopropylcarbinols and Synthetic Support for the Reaction Mechanism

Asymmetric Synthesis of Bioactive Lignans and Enantiomeric Antiviral Activity of Niranthin

Contact Info

Product

Resources

About