Total Synthesis of Aspidofractinine Alkaloid Paucidirinine

Zhang, Weiwei; Lin, Shanhao; Du, Chenglong; Feng, Shangbiao; Liu, Zaimin; Zhang, Jing; Xie, Xingang; Wang, Xiaolei; Li, Huilin; She, Xuegong

doi:10.1021/acs.joc.8b03023

Cited by 16 publications

(9 citation statements)

References 38 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…In 2019, She and coworkers 108 developed the first total synthesis of paucidirinine 244 in 10 steps and 8% overall yield from tryptamine hydrochloride salt. Key steps of this potentially scalable strategy contain a highly stereocontrolled intramolecular [4 + 2] Diels–Alder reaction, an acid-catalyzed lactamization, and a challenging late-stage SmI 2 -induced radical cyclization to construct the bicyclic[2.2.2]octane core.…”

Section: Applications Of Smi 2 -Mediated Reactions...mentioning

confidence: 99%

Samarium(ii) iodide-mediated reactions applied to natural product total synthesis

Heravi

Nazari

2022

RSC Adv.

View full text Add to dashboard Cite

show abstract

Section: Applications Of Smi 2 -Mediated Reactions...mentioning

confidence: 99%

Samarium(ii) iodide-mediated reactions applied to natural product total synthesis

Heravi

Nazari

2022

RSC Adv.

View full text Add to dashboard Cite

show abstract

“…[ 12 ] Its novel structural feature and potent biological activity attracted us and a program towards its chemical synthesis started in our group. [ 13 ] As shown in Scheme 4, the key tetracyclic core 20 was efficiently constructed by a cascade retro‐ aza ‐Michael addition/condensation/intramolecular Diels‐Alder…”

Section: Total Syntheses Of Bioactive Indole Alkaloidsmentioning

confidence: 99%

Concise Total Syntheses of Bioactive Alkaloids Enabled by Development or Application of Cascade Reactions: A Personnel Adventure

Xie

She

2021

Chin. J. Chem.

Self Cite

View full text Add to dashboard Cite

What is the most favorite and original chemistry developed in your research group? Total synthesis of bioactive natural products is the most favorite chemistry in my research group and development or application of new strategies to improve the synthetic efficiency is the most original chemistry developed in my research group. How do you get into this specific field? Could you please share some experiences with our readers? My PhD project was total synthesis of bioactive natural lignans and I devoted myself into synthetic methodology development during my postdoctoral research period. In my opinion, a highly efficient synthetic method will greatly shorten the synthetic route and improve its efficiency for a target-oriented total synthesis. On the other hand, target-oriented total synthesis is the best platform to evaluate the practical value of a synthetic method. So I choose total synthesis of natural products and target-oriented synthetic methodology development as my research fields when I began my independent research. How do you supervise your students? When the students start their projects, I discuss the research subjects with them once a month. Every Saturday night we hold a group meeting to learn and discuss the most recent published literatures related to our research. I give more encouragement when the students meet difficulties in their research. Then we try to solve the difficulties together. What is the most important personality for scientific research? In my view, diligence and persistence are the most important personalities for scientific research. What's your hobby? What's your favorite book(s)? Reading. My favorite book is Sapiens-a brief history of humankind. How do you keep balance between research and family? I usually spend six days (from Monday to Saturday) on research work. On Sunday I will cook some delicious food and enjoy it with my family. My wife understands and supports my work very well. She has done a lot for our family.

show abstract

“…SmI 2 thereby promotes both radical and carbanionic processes. An example of this radical‐polar cross‐over process is found in the first total synthesis of paucidirinine, in which a SmI 2 ‐promoted radical cyclization was carried out from a primary iodide 60 upon a vinylogous amide to construct the last quaternary center and thus achieve the cage‐like skeleton 61 of this alkaloid (Scheme a). An analogous C–C bond formation was previously used by Boger to synthesize kopsinine, recruiting a late‐stage SmI 2 ‐mediated transannular radical conjugate addition ( 62 → 63 ) to assemble the core [2.2.2]octane ring system (Scheme b).…”

Section: From Halocompoundsmentioning

confidence: 99%

Radical Reactions in Alkaloid Synthesis: A Perspective from Carbon Radical Precursors

Bonjoch

Diaba

2020

Eur J Org Chem

View full text Add to dashboard Cite

The usefulness of radical reactions in alkaloid synthesis is reviewed from the perspective of the functional groups embedded in the molecular structure of synthetic intermediates, that act as precursors of carbon‐centered radicals in the construction of new C–C bonds. The functional groups featured are alkenes, alkynes, halides (alkyl, vinyl, aryl), xanthates, sulfides, selenides, aldehydes, ketones, carboxylic acid derivatives (selenoesters, haloacetamides), β‐dicarbonyl compounds, and α‐heterosubstituted nitrogen‐compounds. The use of nitrogen‐centered radicals for C–N bond formation is also covered. Among the variety of radical processes applied, the most predominant are the hydride reductive method (Sn, Si), atom transfer radical reactions (Cu, Ru, B), and single‐electron transfer radical reactions promoted by Sm, Ni, Fe, Mn, Ti, and Ag. This review showcases the role radical reactions have played in the recent development of new strategies in alkaloid synthesis, as well as the implementation of new radical procedures in demanding substrates.

show abstract

Total Synthesis of Aspidofractinine Alkaloid Paucidirinine

Cited by 16 publications

References 38 publications

Samarium(ii) iodide-mediated reactions applied to natural product total synthesis

Samarium(ii) iodide-mediated reactions applied to natural product total synthesis

Concise Total Syntheses of Bioactive Alkaloids Enabled by Development or Application of Cascade Reactions: A Personnel Adventure

Radical Reactions in Alkaloid Synthesis: A Perspective from Carbon Radical Precursors

Contact Info

Product

Resources

About