Evidence map›Paper›PMID 34349919›Full record

ArticleChemical science2021

Short, enantioselective, gram-scale synthesis of (-)-zephyranthine.

Yuxiang Zhao, Yanren Zhu, Guolan Ma, Qi Wei, Shaoxiong Yang, Xiaoyu Zeng, Hongbin Zhang, Jingbo Chen

Abstract read
PubMed Full text at PMC Publisher
In one paragraph

Article in Chemical science, 2021. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 2 papers.

0numbers the graph read from it
0cells of the map it votes in
2citing papers in PubMed
–field-weighted citation impact
1 · What the graph read from it

What it found

Each row is one number read from the abstract, on the scale the paper reported it, with its interval. Left of the dashed line favours the treatment, right favours the comparator. Under each row is the sentence it came from. New to these charts? A ten-minute tutorial.

The abstract states no effect estimate the extractor could read, or names no intervention and outcome on the map, so this paper lights no cell and moves no belief. It is still indexed, cited and linked below.

2 · The registry

The trial behind it

Trials whose registry record cites this paper, or whose number appears in the abstract. A trial that started after this paper was published is citing it as background, not reporting it.

Neither the registry nor the abstract names a trial number. If this is a trial report, that itself is worth knowing.

3 · Its place in the literature

Who cites it

2 citing papers in PubMed.

  1. Article
  2. Review
4 · The record

Corrections and comments

PubMed lists nothing against this paper. Absence here is not a guarantee, only a check that was made.

5 · Who and what money

Authors and funding

8 authors.

Yuxiang ZhaoKey Laboratory of Medicinal Chemistry for Natural Resource, Ministry of Education, Yunnan Provincial Center for Research & Development of Natural Products, School of Chemical Science and Technology, Yunnan University Kunming 650091 P. R. China zhanghb@ynu.edu.cn chenjb@ynu.edu.cn.ORCID https://orcid.org/0000-0002-6658-0680
Yanren ZhuKey Laboratory of Medicinal Chemistry for Natural Resource, Ministry of Education, Yunnan Provincial Center for Research & Development of Natural Products, School of Chemical Science and Technology, Yunnan University Kunming 650091 P. R. China zhanghb@ynu.edu.cn chenjb@ynu.edu.cn.
Guolan MaKey Laboratory of Medicinal Chemistry for Natural Resource, Ministry of Education, Yunnan Provincial Center for Research & Development of Natural Products, School of Chemical Science and Technology, Yunnan University Kunming 650091 P. R. China zhanghb@ynu.edu.cn chenjb@ynu.edu.cn.
Qi WeiKey Laboratory of Medicinal Chemistry for Natural Resource, Ministry of Education, Yunnan Provincial Center for Research & Development of Natural Products, School of Chemical Science and Technology, Yunnan University Kunming 650091 P. R. China zhanghb@ynu.edu.cn chenjb@ynu.edu.cn.ORCID https://orcid.org/0000-0002-5463-7328
Shaoxiong YangKey Laboratory of Medicinal Chemistry for Natural Resource, Ministry of Education, Yunnan Provincial Center for Research & Development of Natural Products, School of Chemical Science and Technology, Yunnan University Kunming 650091 P. R. China zhanghb@ynu.edu.cn chenjb@ynu.edu.cn.
Xiaoyu ZengKey Laboratory of Medicinal Chemistry for Natural Resource, Ministry of Education, Yunnan Provincial Center for Research & Development of Natural Products, School of Chemical Science and Technology, Yunnan University Kunming 650091 P. R. China zhanghb@ynu.edu.cn chenjb@ynu.edu.cn.ORCID https://orcid.org/0000-0002-4108-2255
Hongbin ZhangKey Laboratory of Medicinal Chemistry for Natural Resource, Ministry of Education, Yunnan Provincial Center for Research & Development of Natural Products, School of Chemical Science and Technology, Yunnan University Kunming 650091 P. R. China zhanghb@ynu.edu.cn chenjb@ynu.edu.cn.ORCID https://orcid.org/0000-0002-2516-2634
Jingbo ChenKey Laboratory of Medicinal Chemistry for Natural Resource, Ministry of Education, Yunnan Provincial Center for Research & Development of Natural Products, School of Chemical Science and Technology, Yunnan University Kunming 650091 P. R. China zhanghb@ynu.edu.cn chenjb@ynu.edu.cn.ORCID https://orcid.org/0000-0001-7223-7857

Funding

No grant is acknowledged in the PubMed record.

6 · The paper itself

Abstract

A reasonable synthesis design by strategically integrating functional group manipulation into the ring system construction resulted in a short, enantioselective, gram-scale total synthesis of (-)-zephyranthine. The concise route includes a catalytic Michael/Michael cascade for the asymmetric synthesis of a penta-substituted cyclohexane with three contiguous stereogenic centers, a remarkable 8-step one-pot operation to easily assemble the zephyranthine tetracyclic skeleton, the regioselective construction of a double bond in the C ring and an asymmetric dihydroxylation. This synthesis is also flexible and paves a potential path to a variety of cyclohexylamine-fused tricyclic or polycyclic alkaloids.

Identifiers

PMID34349919
PMCPMC8278928

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Registered trials

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Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.