Citation: Jun Chao Shao, Zhi Hua Ye, Hai Xia Lin, Dian Long Wang, Na Han. Synthesis of novel D-seco-taxoids derived from 1-deoxybaccatin Ⅵ[J]. Chinese Chemical Letters, ;2010, 21(11): 1273-1276. doi: 10.1016/j.cclet.2010.07.001 shu

Synthesis of novel D-seco-taxoids derived from 1-deoxybaccatin Ⅵ

Department of Chemistry, Shanghai University, Shanghai 200444, China

Received Date: 15 January 2010

Fund Project: The authors are grateful to the National Natural Science Foundation of China (No.30672506) and Leading Academic Discipline Project of Shanghai Municipal Education Commission (No.J50102).

New D-seco-taxoids were synthesized from 1-deoxybaccatin Ⅵ and their structures were confirmed by ¹H NMR, ¹³C NMR, ESIMS and X-ray crystallography. The key step of the synthesis involved the opening of the oxetane ring under acid and basic conditions in order to obtain new multidrug resistance (MDR) reversal agents and new synthetic precursors of paclitaxel analogues.
- Taxoids,
- 1-Deoxybaecatin Ⅵ,
- Oxetane ring,
- Paclitaxel
1. [1]
  Wenfeng Zang , Yixin Sun , Jingyi Zhang , Yanzhong Hao , Qianhui Jin , Hongying Xiao , Zuo Zhang , Xianbao Shi , Jin Sun , Zhonggui He , Cong Luo , Bingjun Sun . Two-tailed modification module tuned steric-hindrance effect enabling high therapeutic efficacy of paclitaxel prodrug nanoassemblies. Chinese Chemical Letters, 2025, 36(5): 110230-. doi: 10.1016/j.cclet.2024.110230
2. [2]
  Chao Liu , Liming Gong , Yanhong Liu , Shuangqing Wang , Hao Wu , Liqing Chen , Mingji Jin , Zhonggao Gao , Wei Huang . Lipoic acid-locked reduction-responsive core-cross-linked micelles delivering paclitaxel for triple-negative breast cancer treatment. Chinese Chemical Letters, 2025, 36(8): 110570-. doi: 10.1016/j.cclet.2024.110570
3. [3]
  Lin Li , Bingjun Sun , Jin Sun , Lin Chen , Zhonggui He . Binary prodrug nanoassemblies combining chemotherapy and ferroptosis activation for efficient triple-negative breast cancer therapy. Chinese Chemical Letters, 2024, 35(10): 109538-. doi: 10.1016/j.cclet.2024.109538
4. [4]
  Yuan Xiong , Lan-Hui Qin , Bei Zhao , Lei-Zhi Xu , Yu-Fan Fan , Tian Tian , Hai-Rong Zeng , Ting Liu , Jian Huang , Jian-Ming Sun , Zhen-Hao Tian , Guang-Bo Ge . Structure-based design and development of halogenated-naphthalimides as potent hCYP1B1 inhibitors for overcoming paclitaxel resistance. Chinese Chemical Letters, 2025, 36(11): 110812-. doi: 10.1016/j.cclet.2024.110812
5. [5]
  Yixin Sun , Keke Yu , Xiuchun Guo , Lanlan Zong , Zhonggui He , Xiaohui Pu . Three-in-one reduction and acid-ignited micelles amplify antitumor efficacy via precise synergistic delivery of paclitaxel and naringenin. Chinese Chemical Letters, 2025, 36(6): 110393-. doi: 10.1016/j.cclet.2024.110393
6. [6]
  Peiyan Zhu , Yanyan Yang , Hui Li , Jinhua Wang , Shiqing Li . Rh(Ⅲ)‐Catalyzed sequential ring‐retentive/‐opening [4 + 2] annulations of 2H‐imidazoles towards full‐color emissive imidazo[5,1‐a]isoquinolinium salts and AIE‐active non‐symmetric 1,1′‐biisoquinolines. Chinese Chemical Letters, 2024, 35(10): 109533-. doi: 10.1016/j.cclet.2024.109533
7. [7]
  Xiaojuan Lv , Yuting Dong , Hongliang Huang , Dariusz W. Szczepanik , Naoki Aratani , Takahisa Ikeue , Feng Chen , Tao Zhang , Fengxian Qiu , Toshiharu Teranishi , Songlin Xue . Local aromatic ring cleaves the global aromatic ring in hexaphyrin(2.1.2.1.2.1). Chinese Chemical Letters, 2025, 36(7): 110435-. doi: 10.1016/j.cclet.2024.110435
8. [8]
  Guodong Wang , Mengying Jia , Haitao Liu , Yong Liu , Zhiguo Zhang , Xianxiu Xu . Expeditious synthesis and applications of isoquinoline ring-modified Quinap derivatives. Chinese Chemical Letters, 2025, 36(8): 110705-. doi: 10.1016/j.cclet.2024.110705
9. [9]
  Wenling Yuan , Fengli Li , Zhe Chen , Qiaoxin Xu , Zhenhua Guan , Nanyu Yao , Zhengxi Hu , Junjun Liu , Yuan Zhou , Ying Ye , Yonghui Zhang . AbnI: An α-ketoglutarate-dependent dioxygenase involved in brassicicene CH functionalization and ring system rearrangement. Chinese Chemical Letters, 2024, 35(5): 108788-. doi: 10.1016/j.cclet.2023.108788
10. [10]
  Jing-Qi Tao , Shuai Liu , Tian-Yu Zhang , Hong Xin , Xu Yang , Xin-Hua Duan , Li-Na Guo . Photoinduced copper-catalyzed alkoxyl radical-triggered ring-expansion/aminocarbonylation cascade. Chinese Chemical Letters, 2024, 35(6): 109263-. doi: 10.1016/j.cclet.2023.109263
11. [11]
  Yue Sun , Liming Yang , Yaohang Cheng , Guanghui An , Guangming Li . Pd(I)-catalyzed ring-opening arylation of cyclopropyl-α-aminoamides: Access to α-ketoamide peptidomimetics. Chinese Chemical Letters, 2024, 35(6): 109250-. doi: 10.1016/j.cclet.2023.109250
12. [12]
  Qiuyun Li , Yannan Zhu , Yining Wang , Gang Qi , Wen-Juan Hao , Kelu Yan , Bo Jiang . Catalytic CH activation-initiated transdiannulation: An oxygen transfer route to ring-fluorinated tricyclic γ-lactones. Chinese Chemical Letters, 2024, 35(9): 109494-. doi: 10.1016/j.cclet.2024.109494
13. [13]
  Wenyu Gao , Liming Zhang , Chuang Zhao , Lixiang Liu , Xingran Yang , Jinbo Zhao . Controlled semi-Pinacol rearrangement on a strained ring: Efficient access to multi-substituted cyclopropanes by group migration strategy. Chinese Chemical Letters, 2024, 35(9): 109447-. doi: 10.1016/j.cclet.2023.109447
14. [14]
  Rong-Nan Yi , Wei-Min He . Visible light/copper catalysis enabled radial type ring-opening of sulfonium salts. Chinese Chemical Letters, 2025, 36(4): 110787-. doi: 10.1016/j.cclet.2024.110787
15. [15]
  Yuhan Zhang , Xiao-Lin Zhang , Han Ding , Yuan Xu , Xue-Wei Liu . Catalytic ring-strain release toward a facial and efficient synthesis of versatile C-glycosides. Chinese Chemical Letters, 2025, 36(7): 110560-. doi: 10.1016/j.cclet.2024.110560
16. [16]
  Xue-Wen Wu , Bin-Bao Wang , Yu Qin , Yong-Xiang Huang , Muhammad Aurang Zeb , Bin Cheng , Xiao-Li Li , Chang-Bo Zheng , Wei-Lie Xiao . Diterpenoids with unexpected 5/6/6-fused ring system and its dimer from Strophioblachia glandulosa. Chinese Chemical Letters, 2025, 36(8): 110584-. doi: 10.1016/j.cclet.2024.110584
17. [17]
  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
18. [18]
  Wen-Rui Li , Ru-Bing Wang , Huiqiang Wang , Jin-Yao Yong , Yu-Huan Li , Shi-Shan Yu , Shuang-Gang Ma . Ring-reorganization strategy for asymmetric synthesis of sesquiterpenoid illihenin A and its antiviral activity evaluation. Chinese Chemical Letters, 2025, 36(11): 110945-. doi: 10.1016/j.cclet.2025.110945
19. [19]
  Yang Gao , Huarui Zhang , Yan Xie , Xinjun Xu , Yahui Liu , Hao Lu , Wenkai Zhang , Yuqiang Liu , Cuihong Li , Zhishan Bo . Effect of fluorination positions at diphenylamino flanking groups on the photovoltaic performance for nonfused ring electron acceptors. Chinese Chemical Letters, 2026, 37(1): 111622-. doi: 10.1016/j.cclet.2025.111622
20. [20]
  Yi Zhang , Yong Chen , Qian Wang , Jian-Qiu Li , Song-En Liu , Yu Liu . Slide ring polymer in situ cross-linked conductive ionogel for self-powered sensor. Chinese Chemical Letters, 2026, 37(2): 111676-. doi: 10.1016/j.cclet.2025.111676

Get Citation

PDF

XML

Metrics

PDF Downloads(7)
Abstract views(1281)
HTML views(52)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142

Address：Zhongguancun North First Street 2,100190 Beijing, PR China Tel: +86-010-82449177-888

DownLoad: Full-Size Img PowerPoint

Return