Asymmetric Total Synthesis of Janthinoid A

The asymmetric total synthesis of janthinoid A has been accomplished for the first time in 14 steps without using a protecting group. The <i>trans</i>-decalin subunit and the rigid oxabicyclo[3.2.1]octane motif were constructed via an epoxide-initiated cationic π-cyclization reaction and a Fe(ClO<sub>4</sub>)<sub>3</sub>-mediated oxidative cascade cyclization reaction, respectively.

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Publication Details

Journal
Journal of the American Chemical Society
Published
2025-02-03
DOI
https://doi.org/10.1021/jacs.4c17480
Citations
9
Primary Topic
Traditional and Medicinal Uses of Annonaceae
Type
article
Field-Weighted Citation Impact
10.01

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article

Asymmetric Total Synthesis of Janthinoid A

Zuwei Song, Zihao Zhou, Zhen Jun Yang, Yuanhe Li et al.
9 citations
Journal of the American Chemical Society
Traditional and Medicinal Uses of Annonaceae
10.01
article

Asymmetric Total Synthesis of Janthinoid A

Zuwei Song, Zihao Zhou, Zhen Jun Yang, Yuanhe Li, Fu Tang, Zhongchao Zhang, Jiajun Chen
article en
9 citations

Abstract

The asymmetric total synthesis of janthinoid A has been accomplished for the first time in 14 steps without using a protecting group. The <i>trans</i>-decalin subunit and the rigid oxabicyclo[3.2.1]octane motif were constructed via an epoxide-initiated cationic π-cyclization reaction and a Fe(ClO<sub>4</sub>)<sub>3</sub>-mediated oxidative cascade cyclization reaction, respectively.

Journal of the American Chemical SocietyVol. 147(6)
Peking University (CN), Shenzhen Bay Laboratory (CN), Beijing National Laboratory for Molecular Sciences (CN), Peking University Shenzhen Hospital (CN), State Key Laboratory of Chemical Engineering (CN), Center for Life Sciences (CN)
National Natural Science Foundation of China, Natural Science Foundation of Guangdong Province, Science, Technology and Innovation Commission of Shenzhen Municipality, Shenzhen-Hong Kong Institute of Brain Science, Shenzhen Bay Laboratory
Openalex Percentile: Top 2%
Traditional and Medicinal Uses of Annonaceae
10.01
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