Citation: Shanxiang Liu, Jinxin Wang, Yuyong Ma, Xin Cao, Wei-Dong Zhang, Ang Li. Construction of alkyl-substituted 7-norbornenones through Diels−Alder cycloaddition of electron-deficient olefins and a cyclopentadienone derivative generated in situ[J]. Chinese Chemical Letters, ;2022, 33(4): 2041-2043. doi: 10.1016/j.cclet.2021.09.030 shu

Construction of alkyl-substituted 7-norbornenones through Diels−Alder cycloaddition of electron-deficient olefins and a cyclopentadienone derivative generated in situ

Shanxiang Liu ^{a, b, c} ,
Jinxin Wang ^{b, d, *,} ,
Yuyong Ma ^b ,
Xin Cao ^b ,
Wei-Dong Zhang ^{a, d, *,} ,
Ang Li ^{b, c, *,}

a.
School of Traditional Chinese Pharmacy, China Pharmaceutical University, Nanjing 211198, China
b.
State Key Laboratory of Bioorganic and Natural Products Chemistry, Center for Excellence in Molecular Synthesis, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, University of Chinese Academy of Sciences, Shanghai 200032, China
c.
State Key Laboratory of Innovative Natural Medicine and Traditional Chinese Medicine Injections, Jiangxi Qingfeng Pharmaceutical Co. Ltd., Ganzhou 341000, China
d.
Department of Phytochemistry, School of Pharmacy, Second Military Medical University, Shanghai 200433, China

jxwang2013@126.com

wdzhangy@hotmail.com

ali@sioc.ac.cn

Received Date: 26 June 2021
Revised Date: 4 September 2021
Accepted Date: 7 September 2021
Available Online: 12 September 2021

Figures(3)

Dimeric sesquiterpenoids possessing densely substituted 7-norbornenone/7-norbornenol motifs pose a considerable challenge for chemical synthesis. From a strategic perspective, one could envision intermolecular Diels−Alder cycloaddition as a straightforward method for assembling alkyl-substituted 7-norbornenones. However, this approach is hindered by lability of the required dienes, namely alkyl-substituted cyclopentadienones. Here we report a one-pot protocol for construction of alkyl-substituted 7-norbornenones from electron-deficient olefins and a cyclopentenone derivative. DDQ was found to be an effective oxidant for generating a cyclopentadienone intermediate in situ from the enone. A series of sterically congested 7-norbornenone-containing polycyclic compounds were prepared by using this protocol.
- 7-Norbornenone,
- Alkyl-substituted cyclopentadienone,
- Diels−Alder cycloaddition,
- Dimeric sesquiterpenoid
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