J Am Chem Soc September 2019 PMID 31276619

Asymmetric Total Synthesis of Arcutinidine, Arcutinine, and Arcutine.

Shupeng Zhou, Kaifu Xia, Xuebing Leng, Ang Li

Mentions

23
Peak: 18 in Jul 2019
across 3 sources since Jul 2019

Extended reach

92,616
potential audience

Total likes

221

Video views

9,473

Mentions per month

Jul 2019 – Sep 2022

Where it's discussed

  • X / Twitter19 posts
  • YouTube2 videos
  • Blogs2 articles

AI synopsis

What people are saying

The discussions demonstrate strong interest and engagement through mentions of podcasts, analyses, and comparisons of the synthesis by Ang Li's group with other laboratories, indicating a lively and attentive community focused on the significance and methods of this complex chemical synthesis.

AgreementModerate agreement

Most discussions acknowledge the significance of the synthesis work, reflecting general agreement on its importance in organic chemistry.

InterestHigh interest

Posts show high interest, especially with mentions of podcasts, analyses, and comparisons with other labs, indicating curiosity and engagement.

EngagementModerate engagement

Posts include references to detailed discussions, such as analyses on YouTube and podcasts, suggesting active engagement with the research.

ImpactModerate impact

The focus on comparing synthesis methods and highlighting its significance in the field shows recognition of the research’s influence.

Abstract in brief

  • The researchers successfully carried out the asymmetric total synthesis of three arcutine-type C20 diterpenoid alkaloids—arcutinidine, arcutinine, and arcutine—using a series of strategic reactions.
  • They constructed a pentacyclic intermediate efficiently via two Diels-Alder reactions and developed a cascade sequence involving Prins cyclization and Wagner-Meerwein rearrangement to form the core structure of arcutinidine, which was further elaborated into a more complex oxygenated pentacycle through a scalable process.
  • The synthesis included a chemoselective reductive amination step that produced a pyrroline motif, and the structure of arcutine was confirmed by chemical synthesis and crystallography, clarifying the configuration around the acyl group's carbon.]

Top posts

Most liked on X and Bluesky
The Cyclo Edition
@TheCycloEdition · X

The Cyclo Edition episode #4 is out on Youtube, Spotify, and Apple Podcasts! In this episode we analyze the total synthesis by the lab of Ang Li and compare it to recent syntheses completed by the Sarpong and Qin labs. #chemtwitter https://t.co/7rn1SGKy1a https://t.co/5Ka9yjyhMq

Jul 22, 2019 · 25 likes · 5 shares · 1,235 followers View post →
The Cyclo Edition
@TheCycloEdition · X

Our next podcast is covering the total synthesis of arcutinidine by the group of Ang Li at the Shanghai Institute of Organic Chemistry. Stay tuned for our release tomorrow, Monday, July 22nd! @J_A_C_S https://t.co/3AbAVfKmkv

Jul 21, 2019 · 16 likes · 6 shares · 1,234 followers View post →
Drug Discovery and Synthesis Highlights
@TotalSyntheses · X

Asymmetric Total Synthesis of Arcutinidine, Arcutinine, and Arcutine https://t.co/1eaSm0c80g https://t.co/mqdakLNcib

Aug 23, 2019 · 2 likes · 7,382 followers View post →
有機化学を学ぶ人
@yuukiwomanabu · X

Ang Li新作。不斉全合成。かなり初段階の段階でtBuLiつかってしかもホルミル化っていうのが少し課題に思えました。 #学ぶの論文紹介 Asymmetric Total Synthesis of Arcutinidine, Arcutinine, and Arcutine https://t.co/9oF3Ay9ze3

Sep 2, 2019 · 1 like · 6,516 followers View post →
Total Synthesis
@TotalSynthesis · X

RT @TheCycloEdition: Episode 4 discusses the synthesis of arcutinidine by the group of Ang Li. Within the last few months, this molecule wa…

Jul 27, 2019 · 5 shares · 17,320 followers View post →
Tehshik Yoon
@TehshikYoon · X

RT @TheCycloEdition: Episode 4 discusses the synthesis of arcutinidine by the group of Ang Li. Within the last few months, this molecule wa…

Jul 27, 2019 · 5 shares · 13,775 followers View post →

All mentions

有機化学を学ぶ人
@yuukiwomanabu · X

Ang Li新作。不斉全合成。かなり初段階の段階でtBuLiつかってしかもホルミル化っていうのが少し課題に思えました。 #学ぶの論文紹介 Asymmetric Total Synthesis of Arcutinidine, Arcutinine, and Arcutine https://t.co/9oF3Ay9ze3

Sep 2, 2019 · 1 like · 6,516 followers View post →
Drug Discovery and Synthesis Highlights
@TotalSyntheses · X

Asymmetric Total Synthesis of Arcutinidine, Arcutinine, and Arcutine https://t.co/1eaSm0c80g https://t.co/mqdakLNcib

Aug 23, 2019 · 2 likes · 7,382 followers View post →
Alex Zhurakovskyi
@zhorakovsky · X

RT @TheCycloEdition: Episode 4 discusses the synthesis of arcutinidine by the group of Ang Li. Within the last few months, this molecule wa…

Jul 28, 2019 · 5 shares · 1,295 followers View post →
Wesley Swords
@DrSwordsChem · X

RT @TheCycloEdition: Episode 4 discusses the synthesis of arcutinidine by the group of Ang Li. Within the last few months, this molecule wa…

Jul 27, 2019 · 5 shares · 145 followers View post →
Total Synthesis
@TotalSynthesis · X

RT @TheCycloEdition: Episode 4 discusses the synthesis of arcutinidine by the group of Ang Li. Within the last few months, this molecule wa…

Jul 27, 2019 · 5 shares · 17,320 followers View post →
Tehshik Yoon
@TehshikYoon · X

RT @TheCycloEdition: Episode 4 discusses the synthesis of arcutinidine by the group of Ang Li. Within the last few months, this molecule wa…

Jul 27, 2019 · 5 shares · 13,775 followers View post →
Grace Lutovsky
@grace_lutovsky · X

RT @TheCycloEdition: Episode 4 discusses the synthesis of arcutinidine by the group of Ang Li. Within the last few months, this molecule wa…

Jul 27, 2019 · 5 shares · 371 followers View post →
Shubhendu Karandikar
@ShubhenduKaran1 · X

RT @TheCycloEdition: The Cyclo Edition episode #4 is out on Youtube, Spotify, and Apple Podcasts! In this episode we analyze the total synt…

Jul 23, 2019 · 5 shares · 111 followers View post →
Wesley Swords
@DrSwordsChem · X

RT @TheCycloEdition: The Cyclo Edition episode #4 is out on Youtube, Spotify, and Apple Podcasts! In this episode we analyze the total synt…

Jul 22, 2019 · 5 shares · 145 followers View post →
Grace Lutovsky
@grace_lutovsky · X

RT @TheCycloEdition: The Cyclo Edition episode #4 is out on Youtube, Spotify, and Apple Podcasts! In this episode we analyze the total synt…

Jul 22, 2019 · 5 shares · 371 followers View post →
Tehshik Yoon
@TehshikYoon · X

RT @TheCycloEdition: The Cyclo Edition episode #4 is out on Youtube, Spotify, and Apple Podcasts! In this episode we analyze the total synt…

Jul 22, 2019 · 5 shares · 13,775 followers View post →
Dr. James Mousseau
@J2_Mousseau · X

RT @TheCycloEdition: The Cyclo Edition episode #4 is out on Youtube, Spotify, and Apple Podcasts! In this episode we analyze the total synt…

Jul 22, 2019 · 5 shares · 577 followers View post →
The Cyclo Edition
@TheCycloEdition · X

The Cyclo Edition episode #4 is out on Youtube, Spotify, and Apple Podcasts! In this episode we analyze the total synthesis by the lab of Ang Li and compare it to recent syntheses completed by the Sarpong and Qin labs. #chemtwitter https://t.co/7rn1SGKy1a https://t.co/5Ka9yjyhMq

Jul 22, 2019 · 25 likes · 5 shares · 1,235 followers View post →
Grace Lutovsky
@grace_lutovsky · X

RT @TheCycloEdition: Our next podcast is covering the total synthesis of arcutinidine by the group of Ang Li at the Shanghai Institute of O…

Jul 21, 2019 · 6 shares · 371 followers View post →
Susannah Coote
@suscoote · X

RT @TheCycloEdition: Our next podcast is covering the total synthesis of arcutinidine by the group of Ang Li at the Shanghai Institute of O…

Jul 21, 2019 · 6 shares · 2,167 followers View post →
Tehshik Yoon
@TehshikYoon · X

RT @TheCycloEdition: Our next podcast is covering the total synthesis of arcutinidine by the group of Ang Li at the Shanghai Institute of O…

Jul 21, 2019 · 6 shares · 13,756 followers View post →
AJ Boydston
@aj_boydston · X

RT @TheCycloEdition: Our next podcast is covering the total synthesis of arcutinidine by the group of Ang Li at the Shanghai Institute of O…

Jul 21, 2019 · 6 shares · 2,272 followers View post →
Wesley Swords
@DrSwordsChem · X

RT @TheCycloEdition: Our next podcast is covering the total synthesis of arcutinidine by the group of Ang Li at the Shanghai Institute of O…

Jul 21, 2019 · 6 shares · 144 followers View post →
The Cyclo Edition
@TheCycloEdition · X

Our next podcast is covering the total synthesis of arcutinidine by the group of Ang Li at the Shanghai Institute of Organic Chemistry. Stay tuned for our release tomorrow, Monday, July 22nd! @J_A_C_S https://t.co/3AbAVfKmkv

Jul 21, 2019 · 16 likes · 6 shares · 1,234 followers View post →