Total synthesis of (±)-simonsol C using dearomatization as key reaction under acidic conditions.

Xiao-Yang Bi, Xiao-Shuai Yang, Shan-Shan Chen, Jia-Jun Sui, Zhao-Nan Cai, Yong-Ming Chuan, Hong-Bo Qin

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Article in Beilstein journal of organic chemistry, 2025. 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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5 · Who and what money

Authors and funding

7 authors.

Xiao-Yang BiSchool of Chemistry and Environment, Yunnan Minzu University, Kunming 650000, China.

Xiao-Shuai YangSchool of Chemistry and Environment, Yunnan Minzu University, Kunming 650000, China.

Shan-Shan ChenSchool of Chemistry and Environment, Yunnan Minzu University, Kunming 650000, China.

Jia-Jun SuiSchool of Chemistry and Environment, Yunnan Minzu University, Kunming 650000, China.

Zhao-Nan CaiSchool of Chemistry and Environment, Yunnan Minzu University, Kunming 650000, China.

Yong-Ming ChuanSchool of Chemistry and Environment, Yunnan Minzu University, Kunming 650000, China.ORCID https://orcid.org/0000-0003-3394-8618

Hong-Bo QinSchool of Chemistry and Environment, Yunnan Minzu University, Kunming 650000, China.ORCID https://orcid.org/0000-0003-2603-9520

Funding

No grant is acknowledged in the PubMed record.

6 · The paper itself

Abstract

The total synthesis of (±)-simonsol C was accomplished using a dearomatization under acidic conditions as key step to construct an aryl-containing quaternary center. The 6/5/6 benzofuran unit was formed through reductive elimination with Zn/AcOH and a spontaneous oxy-Michael addition. This synthesis consists of 8 steps and achieves an overall yield of 13%, making it the shortest known route.

Indexed as

acidic dearomazationbenzofuran(±)-simonsol Ctotal synthesis

Identifiers

PMID40130178

DOI10.3762/bjoc.21.47

PMCPMC11931641

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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.