Citation: Bin YE, Jin Li ZHANG, Ming Qing CHEN, Yu Lin WU. SYNTHESIS OF 1, 6-DIEPI-DIHYDROARTEANNUIC ACID[J]. Chinese Chemical Letters, ;1990, 1(1): 65-68. shu

SYNTHESIS OF 1, 6-DIEPI-DIHYDROARTEANNUIC ACID

a Shanghai Institute of Organic Chemistry Academia Sinica Shanghai 200032;
b Research Center of Analysis and Measurement Fudan University

Received Date: 13 December 1989

R(+)-Citronellal was converted into a key intermediate, (unsaturated ketone 5)in three steps, which led to 6 having the frame of arteannuic acid through intramolecular ene reaction.Further modification of 6afforded 1, 6-epimer of dihydroarteannuic acid.The configuration of 7 was determined by X-ray diffraction analysis.
1. [1]
  Zan Chen , Yi Wang , Yuxuan Zhou , Yunlang Li , Rong Xiong , Wenting Huang , Huanfeng Jiang , Wanqing Wu . Selective synthesis of [6-6-7]/[6-6-6] core polycyclic heterocycles via Lewis acid-mediated cascade annulation of 1,6-enynols with aminonitriles. Chinese Chemical Letters, 2026, 37(6): 111718-. doi: 10.1016/j.cclet.2025.111718
2. [2]
  Zhen Liu , Zhi-Yuan Ren , Chen Yang , Xiangyi Shao , Li Chen , Xin Li . Asymmetric alkenylation reaction of benzoxazinones with diarylethylenes catalyzed by B(C₆F₅)₃/chiral phosphoric acid. Chinese Chemical Letters, 2024, 35(5): 108939-. doi: 10.1016/j.cclet.2023.108939
3. [3]
  Wenyi Mei , Lijuan Xie , Xiaodong Zhang , Cunjian Shi , Fengzhi Wang , Qiqi Fu , Zhenjiang Zhao , Honglin Li , Yufang Xu , Zhuo Chen . Design, synthesis and biological evaluation of fluorescent derivatives of ursolic acid in living cells. Chinese Chemical Letters, 2024, 35(5): 108825-. doi: 10.1016/j.cclet.2023.108825
4. [4]
  Weizhong LING , Jingyi LIN , Jianglin ZHU , Yuyi LIANG , Shanshan DAI , Yu LI . Syntheses, structures, and catalytic performances of complexes with 4,4′-dihydroxy-[1,1′-biphenyl]-3,3′-dicarboxylic acid ligands. Chinese Journal of Inorganic Chemistry, 2026, 42(1): 152-160. doi: 10.11862/CJIC.20250204
5. [5]
  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
6. [6]
  Juntao Cai , Qian Wang , Xu Shen , Lifeng Zhu , Shiqing Jiang , Jian Yin , Chunhong Dong . Chemical strategies for the stereoselective construction of 1,2-cis-galacturonic and aminogalacturonic acid glycosides. Chinese Chemical Letters, 2026, 37(5): 112235-. doi: 10.1016/j.cclet.2025.112235
7. [7]
  Xiaoya Zhuo , Xiangwen Tan , Yi Wang , Wanqing Wu , Huanfeng Jiang . Palladium catalyzed tandem Heck/Tsuji-Trost and 6-endo cyclization reactions of aryl iodides, vinylacetic acid, and aryl amines. Chinese Chemical Letters, 2026, 37(6): 111777-. doi: 10.1016/j.cclet.2025.111777
8. [8]
  Zhengzheng LIU , Pengyun ZHANG , Chengri WANG , Shengli HUANG , Guoyu YANG . Synthesis, structure, and electrochemical properties of a sandwich-type {Co₆}-cluster-added germanotungstate. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1173-1179. doi: 10.11862/CJIC.20240039
9. [9]
  Shuwen SUN , Gaofeng WANG . Design and synthesis of a Zn(Ⅱ)-based coordination polymer as a fluorescent probe for trace monitoring 2, 4, 6-trinitrophenol. Chinese Journal of Inorganic Chemistry, 2025, 41(4): 753-760. doi: 10.11862/CJIC.20240399
10. [10]
  Wenya DING , Fangfei XU , Jiayu GU , Xinran CHEN , Kai CHEN . Synthesis and crystal structure of three cucurbit[6]uril-cadmium supramolecular assemblies. Chinese Journal of Inorganic Chemistry, 2026, 42(4): 808-816. doi: 10.11862/CJIC.20260012
11. [11]
  Zhiwei Chen , Heyun Sheng , Xue Li , Menghan Chen , Xin Li , Qiuling Song . Efficient capture of difluorocarbene by pyridinium 1,4-zwitterionic thiolates: A concise synthesis of difluoromethylene-containing 1,4-thiazine derivatives. Chinese Chemical Letters, 2024, 35(4): 108937-. doi: 10.1016/j.cclet.2023.108937
12. [12]
  Qi Li , Zi-Lu Wang , Yun-He Xu . Copper-catalyzed 1,4-silylcyanation of 1,3-enynes: A silyl radical-initiated approach for synthesis of difunctionalized allenes. Chinese Chemical Letters, 2025, 36(3): 109991-. doi: 10.1016/j.cclet.2024.109991
13. [13]
  Haitao Yin , Liang Meng , Li Li , Jiamu Xiao , Longrui Liang , Nannan Huang , Yansong Shi , Angang Zhao , Jingwen Hou . Polydopamine-modified biochar supported polylactic acid and zero-valent iron affects the functional microbial community structure for 1,1,1-trichloroethane removal in simulated groundwater. Chinese Chemical Letters, 2025, 36(1): 110313-. doi: 10.1016/j.cclet.2024.110313
14. [14]
  Yulin Mao , Jingyu Ma , Jiecheng Ji , Yuliang Wang , Wanhua Wu , Cheng Yang . Crown aldoxime ethers: Their synthesis, structure, acid-catalyzed/photo-induced isomerization and adjustable guest binding. Chinese Chemical Letters, 2024, 35(11): 109927-. doi: 10.1016/j.cclet.2024.109927
15. [15]
  Guoping Yang , Zhoufu Lin , Xize Zhang , Jiawei Cao , Xuejiao Chen , Yufeng Liu , Xiaoling Lin , Ke Li . Assembly of Y(Ⅲ)-containing antimonotungstates induced by malic acid with catalytic activity for the synthesis of imidazoles. Chinese Chemical Letters, 2024, 35(12): 110274-. doi: 10.1016/j.cclet.2024.110274
16. [16]
  Dongdong YANG , Jianhua XUE , Yuanyu YANG , Meixia WU , Yujia BAI , Zongxuan WANG , Qi MA . Design and synthesis of two coordination polymers for the rapid detection of ciprofloxacin based on triphenylpolycarboxylic acid ligands. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2466-2474. doi: 10.11862/CJIC.20240266
17. [17]
  Jiajun Lu , Zhehui Liao , Tongxiang Cao , Shifa Zhu . Synergistic Brønsted/Lewis acid catalyzed atroposelective synthesis of aryl-β-naphthol. Chinese Chemical Letters, 2025, 36(1): 109842-. doi: 10.1016/j.cclet.2024.109842
18. [18]
  Jimin HOU , Mengyang LI , Chunhua GONG , Shaozhuang ZHANG , Caihong ZHAN , Hao XU , Jingli XIE . Synthesis, structures, and properties of metal-organic frameworks based on bipyridyl ligands and isophthalic acid. Chinese Journal of Inorganic Chemistry, 2025, 41(3): 549-560. doi: 10.11862/CJIC.20240348
19. [19]
  Nana Yang , Rui Yuan , Xinyue Fu , Xiao Tian , Jin Yu , Shengzhou Ma , Liuqing Wen , Jiabin Zhang . Concise synthesis of NDP-activated uronic acid by an oxidation reaction insertion strategy. Chinese Chemical Letters, 2025, 36(8): 110757-. doi: 10.1016/j.cclet.2024.110757
20. [20]
  Pan Hu , Xiaofan Wu , Yi An , Xianjing Zheng , Liang Gao , Yuan Tao , Yajiao Zhang , Zedu Huang , Fener Chen . Batch and continuous-flow asymmetric synthesis of D-pantothenic acid precursor enabled by immobilized ketoreductase mutant. Chinese Chemical Letters, 2026, 37(2): 111945-. doi: 10.1016/j.cclet.2025.111945

Get Citation

PDF

XML

Metrics

PDF Downloads(2)
Abstract views(1545)
HTML views(47)

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