AbstractMany terpenoids with isoprene unit(s) demonstrating critical biological activities have been isolated and characterized. In this study, we have developed a robust chem‐stamp strategy for the construction of the key isoprene unit, which consists of two steps: one‐carbon extension of aldehydes to the alkenyl boronates by the boron‐Wittig reaction and the rhodium‐catalyzed reaction of alkenyl boronates with 2,3‐allenols to yield enals. This chem‐stamp could readily be applied repeatedly and separately, enabling the modular concise synthesis of many natural and pharmaceutically active terpenoids, including retinal, β‐carotene, vitamin A, tretinoin, fenretinide, acitretin, ALRT1550, nigerapyrone C, peretinoin, and lycopene. Owing to the diversified availability of the starting materials, aldehydes and 2,3‐allenols, creation of new non‐natural terpenoids has been realized from four dimensions: the number of isoprene units, the side chain, and the two terminal groups.

More from our Archive

• DOI: 10.1039/d3tb00505d 2023

  Metal–organic frameworks (MOFs) as apt luminescent probes for the detection of biochemical analytes

  Dongwen Luo, Jiefeng Huang, Yanhong Jian, Ayushi Singh, Abhinav Kumar, Jianqiang Liu, Ying Pan, Qin Ouyang

• DOI: 10.1039/d3ra02485g 2023

  Harnessing the potential of CsPbBr₃-based perovskite solar cells using efficient charge transport materials and global optimization

  M. Khalid Hossain, Sagar Bhattarai, A. A. Arnab, Mustafa K. A. Mohammed, Rahul Pandey, Md Hasan Ali, Md. Ferdous Rahman, Md. Rasidul Islam, D. P. Samajdar, Jaya Madan, H. Bencherif, D. K. Dwivedi, Mongi Amami

• DOI: 10.1002/smll.202303353 2023

  Two Birds One Stone: Graphene Assisted Reaction Kinetics and Ionic Conductivity in Phthalocyanine‐Based Covalent Organic Framework Anodes for Lithium‐ion Batteries

  Jianjun Zhao, Miaomiao Zhou, Jun Chen, Luyi Wang, Qian Zhang, Shengwen Zhong, Haijiao Xie, Yutao Li

• DOI: 10.1039/d2cs00806h 2023

  Carbon nitride based materials: more than just a support for single-atom catalysis

  Guilherme F. S. R Rocha, Marcos A. R. da Silva, Andrea Rogolino, Gabriel A. A. Diab, Luis F. G. Noleto, Markus Antonietti, Ivo F. Teixeira

• DOI: 10.1002/smll.202303156 2023

  Solvent Engineering of Oxygen‐Enriched Carbon Dots for Efficient Electrochemical Hydrogen Peroxide Production

  Xiaoyu Shen, Zeming Wang, Huazhang Guo, Zhendong Lei, Zheng Liu, Liang Wang

• DOI: 10.1039/d2cs00441k 2023

  Spatially and temporally understanding dynamic solid–electrolyte interfaces in carbon dioxide electroreduction

  Jiali Wang, Hui-Ying Tan, Ming-Yu Qi, Jing-Yu Li, Zi-Rong Tang, Nian-Tzu Suen, Yi-Jun Xu, Hao Ming Chen

• DOI: 10.1039/d3ta01766d 2023

  Concurrent alloying and vacancy engineering for intensifying hydrogen spillover towards alcohol–water co-electrolysis

  Hui Xu, Kun Wang, Guangyu He, Haiqun Chen

• DOI: 10.1002/anie.202306680 2023

  Highly Luminescent Lanthanide Metal‐Organic Frameworks with Tunable Color for Nanomolar Detection of Iron(III), Ofloxacin and Gossypol and Anti‐counterfeiting Applications

  Xiaolin Yu, Alexey A. Ryadun, Dmitry I. Pavlov, Tatiana Y. Guselnikova, Andrei S. Potapov, Vladimir P. Fedin

• DOI: 10.1002/smll.202303631 2023

  Synergistic Effect of Electron Scattering and Space Charge Transfer Enabled Unprecedented Room Temperature NO₂ Sensing Response of SnO₂

  Yajie Zhang, Yadong Jiang, Zhen Yuan, Bohao Liu, Qiuni Zhao, Qi Huang, Ziteng Li, Wen Zeng, Zaihua Duan, Huiling Tai

• DOI: 10.1002/anie.202306881 2023

  2D MOF‐assisted Pyrolysis‐displacement‐alloying Synthesis of High‐entropy Alloy Nanoparticles Library for Efficient Electrocatalytic Hydrogen Oxidation

  Ziming Qiu, Yong Li, Yidan Gao, Zhenyang Meng, Yangyang Sun, Yang Bai, Nian‐Tzu Suen, Hsiao‐Chien Chen, Yecan Pi, Huan Pang