Evidence map›Paper›PMID 34349905›Full record

ArticleChemical science2021

A palladium-catalyzed approach to allenic aromatic ethers and first total synthesis of terricollene A.

Chaofan Huang, Fuchun Shi, Yifan Cui, Can Li, Jie Lin, Qi Liu, Anni Qin, Huanan Wang, Guolin Wu, Penglin Wu and 8 more

Abstract read
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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. Not yet cited in PubMed.

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0citing papers in PubMed
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1 · What the graph read from it

What it found

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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

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3 · Its place in the literature

Who cites it

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No citing paper in PubMed yet.

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

18 authors.

Chaofan HuangResearch Center for Molecular Recognition and Synthesis, Department of Chemistry, Fudan University 220 Handan Lu Shanghai 200433 P. R. China.
Fuchun ShiState Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences 345 Lingling Lu Shanghai 200032 P. R. China masm@sioc.ac.cn.
Yifan CuiState Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences 345 Lingling Lu Shanghai 200032 P. R. China masm@sioc.ac.cn.
Can LiState Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences 345 Lingling Lu Shanghai 200032 P. R. China masm@sioc.ac.cn.
Jie LinResearch Center for Molecular Recognition and Synthesis, Department of Chemistry, Fudan University 220 Handan Lu Shanghai 200433 P. R. China.
Qi LiuResearch Center for Molecular Recognition and Synthesis, Department of Chemistry, Fudan University 220 Handan Lu Shanghai 200433 P. R. China.
Anni QinResearch Center for Molecular Recognition and Synthesis, Department of Chemistry, Fudan University 220 Handan Lu Shanghai 200433 P. R. China.
Huanan WangResearch Center for Molecular Recognition and Synthesis, Department of Chemistry, Fudan University 220 Handan Lu Shanghai 200433 P. R. China.
Guolin WuResearch Center for Molecular Recognition and Synthesis, Department of Chemistry, Fudan University 220 Handan Lu Shanghai 200433 P. R. China.
Penglin WuResearch Center for Molecular Recognition and Synthesis, Department of Chemistry, Fudan University 220 Handan Lu Shanghai 200433 P. R. China.
Junzhe XiaoState Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences 345 Lingling Lu Shanghai 200032 P. R. China masm@sioc.ac.cn.ORCID https://orcid.org/0000-0003-2361-3507
Haibo XuState Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences 345 Lingling Lu Shanghai 200032 P. R. China masm@sioc.ac.cn.
Yuan YuanResearch Center for Molecular Recognition and Synthesis, Department of Chemistry, Fudan University 220 Handan Lu Shanghai 200433 P. R. China.
Yizhan ZhaiState Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences 345 Lingling Lu Shanghai 200032 P. R. China masm@sioc.ac.cn.
Wei-Feng ZhengResearch Center for Molecular Recognition and Synthesis, Department of Chemistry, Fudan University 220 Handan Lu Shanghai 200433 P. R. China.
Yangguangyan ZhengResearch Center for Molecular Recognition and Synthesis, Department of Chemistry, Fudan University 220 Handan Lu Shanghai 200433 P. R. China.ORCID https://orcid.org/0000-0002-0434-3348
Biao YuState Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences 345 Lingling Lu Shanghai 200032 P. R. China masm@sioc.ac.cn.
Shengming MaResearch Center for Molecular Recognition and Synthesis, Department of Chemistry, Fudan University 220 Handan Lu Shanghai 200433 P. R. China.ORCID https://orcid.org/0000-0002-2866-2431

Funding

No grant is acknowledged in the PubMed record.

6 · The paper itself

Abstract

A palladium-catalyzed C-O bond formation reaction between phenols and allenylic carbonates to give 2,3-allenic aromatic ethers with decent to excellent yields under mild reaction conditions has been described. A variety of synthetically useful functional groups are tolerated and the synthetic utility of this method has been demonstrated through a series of transformations of the allene moiety. By applying this reaction as the key step, the total syntheses of naturally occurring allenic aromatic ethers, eucalyptene and terricollene A (first synthesis; 4.5 g gram scale), have been accomplished.

Identifiers

PMID34349905
PMCPMC8278932

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