Total Synthesis of Penicibilaenes Enabled by a Tandem Double Conia-ene Type Reaction

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成果类型：

期刊论文

作者：

Wang, Zheyuan;Song, Zhilin;Huang, Jun;Yang, Zhen

通讯作者：

Yang, Z;Huang, J

作者机构：

[Yang, Zhen; Yang, Z; Wang, Zheyuan; Song, Zhilin] Peking Univ, Shenzhen Grad Sch, State Key Lab Chem Oncogen, Shenzhen 518055, Peoples R China.

[Yang, Zhen; Yang, Z; Wang, Zheyuan; Song, Zhilin] Peking Univ, Shenzhen Grad Sch, Key Lab Chem Genom, Shenzhen 518055, Peoples R China.

[Huang, Jun] Univ South China, Sch Chem & Chem Engn, Hengyang 421001, Peoples R China.

[Yang, Zhen; Yang, Z] Peking Univ, Key Lab Bioorgan Chem & Mol Engn, Beijing Natl Lab Mol Sci, Minist Educ, Beijing 100871, Peoples R China.

[Yang, Zhen; Yang, Z] Peking Univ, Peking Tsinghua Ctr Life Sci, Beijing, Peoples R China.

通讯机构：

[Yang, Z ] P

[Huang, J ] U

Peking Univ, Shenzhen Grad Sch, State Key Lab Chem Oncogen, Shenzhen 518055, Peoples R China.

Peking Univ, Shenzhen Grad Sch, Key Lab Chem Genom, Shenzhen 518055, Peoples R China.

Univ South China, Sch Chem & Chem Engn, Hengyang 421001, Peoples R China.

语种：

英文

期刊：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

ISSN：

0002-7863

年：

2024

卷：

146

期：

页码：

4363-4368

DOI：

10.1021/jacs.3c14614

基金类别：

Science and Technology Program of Hunan Province [21632002, 21572009, 21402002, 22371117]; National Science Foundation of China; Scientific and Technological Innovation Project [2015ASKJ02]; Qingdao National Laboratory for Marine Science and Technology [2022RC1106]; Science and Technology Program of Hunan Province

机构署名：

本校为通讯机构

院系归属：

化学化工学院

摘要：

The total syntheses of penicibilaenes A and B are described. The key step is the (t)BuOK/DMSO-mediated tandem 5-exo-dig Conia-ene type reaction and 6-exo-dig Conia-ene type reaction to install the tricyclic [6.3.1.0(1,5)] dodecane core of penicibilaenes from dibutynyl cyclohexanone in a single step, together with a sequence of copper-mediated conjugate addition and Crabtree's hydrogenation to forge the st...

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Total Synthesis of Penicibilaenes Enabled by a Tandem Double Conia-ene Type Reaction

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