Citation: Mansour Nawasreh. Chemo-and regioselective hydroboration of △^14,15 in certain cephalostatin analogue[J]. Chinese Chemical Letters, ;2008, 19(12): 1391-1394. doi: 10.1016/j.cclet.2008.09.055 shu

Chemo-and regioselective hydroboration of △^14,15 in certain cephalostatin analogue

Mansour Nawasreh

Basic Sciences Department, Faculty of Engineering Technology, Al-Balqa Applied University, P. B. 15008, Marka, 11134 Amman, Jordan

Received Date: 16 April 2008

Fund Project: The author would like to acknowledge the Deutsche Forschungsgemeinschaft DFG for funding this work, which carried out in the laboratories of Professor H. Duddeck, Leibniz University of Hannover, to whom the author is very grateful. The author also acknowledges Professor W. Beil for biological evaluation.

The symmetrical diketone Ⅱ, which can be synthesized in gram scale using a well established method, was used as a starting material to prepare the 11a-methoxy ketomethylene Ⅵ. This is in continuation of our study aiming at the synthesis of multi-hydroxylated cephalostatin analogues, as for example cephalostatin 1 Ⅰ, a potent anti-tumor natural product. Compound Ⅵ underwent chemo- and regioselective hydroboration reaction at only one of △^14,15 double bonds furnishing compound Ⅸ as a major product in a fair yield.
- Cephalostatin 1,
- Diketone,
- Hydroboration of △^14,15double bond,
- Anti-cancer activity
1. [1]
  Yunyan Li , Zimin Cai , Zhicheng Wang , Sifeng Zhu , Wendian Liu , Cheng Wang . Construction of biomimetic hybrid nanovesicles based on M1 macrophage-derived exosomes for therapy of cancer. Chinese Chemical Letters, 2025, 36(4): 109942-. doi: 10.1016/j.cclet.2024.109942
2. [2]
  Xiongbo Song , Jinwen Xiao , Juan Wu , Li Sun , Long Chen . Decellularized amniotic membrane promotes the anti-inflammatory response of macrophages via PI3K/AKT/HIF-1α pathway. Chinese Chemical Letters, 2025, 36(1): 109844-. doi: 10.1016/j.cclet.2024.109844
3. [3]
  Rongrong Zheng , Zuxiao Chen , Qiuyuan Li , Ni Yang , Wenjun Zhang , Chuyu Huang , Linping Zhao , Xin Chen , Hong Cheng , Shiying Li . Endoplasmic reticulum targeting photodynamic oxidizer to boost anti-tumor immunity by intensifying immunogenic cell death in conjunction with IDO1 inhibition. Chinese Chemical Letters, 2025, 36(12): 110865-. doi: 10.1016/j.cclet.2025.110865
4. [4]
  Fuyun Chi , Man Zhang , Yiman Han , Fukui Shen , Shijie Peng , Bo Su , Yuanyuan Hou , Gang Bai . Covalent modulation of mPGES1 activity via α,β-unsaturated aldehyde group: Implications for downregulating PGE2 expression and antipyretic response. Chinese Chemical Letters, 2025, 36(4): 109913-. doi: 10.1016/j.cclet.2024.109913
5. [5]
  Bofei JIA , Zhihao LIU , Zongyuan GAO , Shuai ZHOU , Mengxiang WU , Qian ZHANG , Xiamei ZHANG , Shuzhong CHEN , Xiaohan YANG , Yahong LI . Cu(Ⅱ) and Cu(Ⅰ) complexes based on derivatives of imidazo[1,5-a]pyridine: Synthesis, structures, in situ metal-ligand reactions, and catalytic activity. Chinese Journal of Inorganic Chemistry, 2025, 41(5): 1020-1036. doi: 10.11862/CJIC.20240317
6. [6]
  Yang Liu , Jing Liang , Mengzhu Zheng , Haoze Song , Lixia Chen , Hua Li . PD-L1/SHP2 dual PROTACs inhibit melanoma by enhancing T-cell killing activity. Chinese Chemical Letters, 2025, 36(6): 110317-. doi: 10.1016/j.cclet.2024.110317
7. [7]
  Gen Zhang , Ying Gu , Lin Li , Fuli Ma , Dan Yue , Xiaoguang Zhou , Chungui Tian . Anion-modulated HER and OER activity of 1D Co-Mo based interstitial compound heterojunctions for the effective overall water splitting. Chinese Chemical Letters, 2025, 36(7): 110110-. doi: 10.1016/j.cclet.2024.110110
8. [8]
  Juan He , Jiao-Xian Du , Meng Wang , Xiao-Dong Luo , Tao Feng . Irpexlactones A and B, a pair of ring-rearranged tremulane sesquiterpenoids from the basidiomycete Irpex lacteus and their anti-inflammatory activity. Chinese Chemical Letters, 2025, 36(10): 110769-. doi: 10.1016/j.cclet.2024.110769
9. [9]
  Qiang Li , Jiangbo Fan , Hongkai Mu , Lin Chen , Yongzhen Yang , Shiping Yu . Nucleus-targeting orange-emissive carbon dots delivery adriamycin for enhanced anti-liver cancer therapy. Chinese Chemical Letters, 2024, 35(6): 108947-. doi: 10.1016/j.cclet.2023.108947
10. [10]
  Ying Sun , Minglong Chen , Ying Chen , Wanchen Zhao , Yanping Fu , Zhengwei Huang , Chao Lu , Chuanbin Wu , Xin Pan , Guilan Quan . Dissolving microneedle-assisted in situ cancer vaccine combined with cytolytic peptide for anti-melanoma immunotherapy. Chinese Chemical Letters, 2025, 36(12): 110908-. doi: 10.1016/j.cclet.2025.110908
11. [11]
  Yulong Shi , Fenbei Chen , Mengyuan Wu , Xin Zhang , Runze Meng , Kun Wang , Yan Wang , Yuheng Mei , Qionglu Duan , Yinghong Li , Rongmei Gao , Yuhuan Li , Hongbin Deng , Jiandong Jiang , Yanxiang Wang , Danqing Song . Chemical construction and anti-HCoV-OC43 evaluation of novel 10,12-disubstituted aloperine derivatives as dual cofactor inhibitors of TMPRSS2 and SR-B1. Chinese Chemical Letters, 2024, 35(5): 108792-. doi: 10.1016/j.cclet.2023.108792
12. [12]
  Yunli Xu , Xuwen Da , Lei Wang , Yatong Peng , Wanpeng Zhou , Xiulian Liu , Yao Wu , Wentao Wang , Xuesong Wang , Qianxiong Zhou . Ru(Ⅱ)-based aggregation-induced emission (AIE) agents with efficient ¹O₂ generation, photo-catalytic NADH oxidation and anticancer activity. Chinese Chemical Letters, 2025, 36(5): 110168-. doi: 10.1016/j.cclet.2024.110168
13. [13]
  Bin Dong , Ning Yu , Qiu-Yue Wang , Jing-Ke Ren , Xin-Yu Zhang , Zhi-Jie Zhang , Ruo-Yao Fan , Da-Peng Liu , Yong-Ming Chai . Double active sites promoting hydrogen evolution activity and stability of CoRuOH/Co₂P by rapid hydrolysis. Chinese Chemical Letters, 2024, 35(7): 109221-. doi: 10.1016/j.cclet.2023.109221
14. [14]
  Zhirong Yang , Shan Wang , Ming Jiang , Gengchen Li , Long Li , Fangzhi Peng , Zhihui Shao . One stone three birds: Ni-catalyzed asymmetric allenylic substitution of allenic ethers, hydroalkylation of 1,3-enynes and double alkylation of enynyl ethers. Chinese Chemical Letters, 2024, 35(8): 109518-. doi: 10.1016/j.cclet.2024.109518
15. [15]
  Wenjia Wang , Xingyue He , Xiaojie Wang , Tiantian Zhao , Osamu Muraoka , Genzoh Tanabe , Weijia Xie , Tianjiao Zhou , Lei Xing , Qingri Jin , Hulin Jiang . Glutathione-depleted cyclodextrin pseudo-polyrotaxane nanoparticles for anti-inflammatory oxaliplatin (Ⅳ) prodrug delivery and enhanced colorectal cancer therapy. Chinese Chemical Letters, 2024, 35(4): 108656-. doi: 10.1016/j.cclet.2023.108656
16. [16]
  Wujun Jian , Mong-Feng Chiou , Yajun Li , Hongli Bao , Song Yang . Cu-catalyzed regioselective diborylation of 1,3-enynes for the efficient synthesis of 1,4-diborylated allenes. Chinese Chemical Letters, 2024, 35(5): 108980-. doi: 10.1016/j.cclet.2023.108980
17. [17]
  Chunhua Ma , Mengjiao Liu , Siyu Ouyang , Zhenwei Cui , Jingjing Bi , Yuqin Jiang , Zhiguo Zhang . Metal-free construction of diverse 1,2,4-triazolo[1,5-a]pyridines on water. Chinese Chemical Letters, 2025, 36(1): 109755-. doi: 10.1016/j.cclet.2024.109755
18. [18]
  Liangfeng Yang , Liang Zeng , Yanping Zhu , Qiuan Wang , Jinheng Li . Copper-catalyzed photoredox 1,4-amidocyanation of 1,3-enynes with N-amidopyridin-1-ium salts and TMSCN: Facile access to α-amido allenyl nitriles. Chinese Chemical Letters, 2024, 35(11): 109685-. doi: 10.1016/j.cclet.2024.109685
19. [19]
  . 第41卷第1期封面和目次. Acta Physico-Chimica Sinica, 2025, 41(1): -.
20. [20]
  Huiju Cao , Lei Shi . sp¹-Hybridized linear and cyclic carbon chain. Chinese Chemical Letters, 2025, 36(4): 110466-. doi: 10.1016/j.cclet.2024.110466