Synthesis of annonaceous acetogenin (4S,5S) and (4S,5R)-muricatacin as well as confirmation of absolute configuration of the tetrahydrofuran segment of annonacin

Acta Chimica Sinica ›› 1992, Vol. 50 ›› Issue (9): 901-904. Previous Articles Next Articles

Original Articles

番荔枝皂素(4S,5S)和(4S,5R)-Muricatacin的合成及Annonacin四氢呋喃段绝对构型的确证

姚祝军;张一兵;吴毓林

中国科学院上海有机化学研究所;中国科学院生命有机化学国家重点实验室

发布日期:1992-09-15

Synthesis of annonaceous acetogenin (4S,5S) and (4S,5R)-muricatacin as well as confirmation of absolute configuration of the tetrahydrofuran segment of annonacin

YAO ZHUJUN;ZHANG YIBING;WU YULIN

Published:1992-09-15

Abstract

The synthesis of (+)-(4S,5S)-muricatacin (I) and its (4S,5R) isomer from L-(+)-glutamic acid as starting material is reported. Natural muricatacin is confirmed as a threo mixture major in (4R,5R) configuration and hence the absolute configuration of the THF segment of annonacin is (15R,16R,19R,20R) by comparison of the NMR and optical rotations.

Key words: NMR SPECTROMETRY, REDUCTION, GLUTAMIC ACID, TETRAHYDROFURAN P, ABSOLUTE CONFIGURATION

CLC Number:

O629

Cite this article

YAO ZHUJUN;ZHANG YIBING;WU YULIN. Synthesis of annonaceous acetogenin (4S,5S) and (4S,5R)-muricatacin as well as confirmation of absolute configuration of the tetrahydrofuran segment of annonacin[J]. Acta Chimica Sinica, 1992, 50(9): 901-904.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

[1]	Ping Li, Qiyu Yang, Jing Zeng, Ran Zhang, Qiuyan Chen, Fei Yan. Effect of Fluorine Doping on the Performance of Reversible Solid Oxide Cells and Related Kinetic Studies [J]. Acta Chimica Sinica, 2024, 82(1): 36-45.
[2]	Yuhan Wu, Dongdong Zhang, Hongyu Yin, Zhengnan Chen, Wen Zhao, Yuhua Chi. Density Functional Theory Study of Janus In₂S₂X Photocatalytic Reduction of CO₂ under “Double Carbon” Target [J]. Acta Chimica Sinica, 2023, 81(9): 1148-1156.
[3]	Wei Hou, Yancai Yao, Lizhi Zhang. Advances in Electrochemical Reductive Removal of Oxyanions in Water^★ [J]. Acta Chimica Sinica, 2023, 81(8): 979-989.
[4]	Jianchuan Liu, Cuiyan Li, Yaozu Liu, Yujie Wang, Qianrong Fang. Highly-Stable Two-Dimensional Bicarbazole-based sp²-Carbon-conjugated Covalent Organic Framework for Efficient Electrocatalytic Oxygen Reduction^★ [J]. Acta Chimica Sinica, 2023, 81(8): 884-890.
[5]	Jia Liu, Guanghai Chen, Yiqun Chen, Jietao Jiang, Xiao Xiao, Qiang Wu, Lijun Yang, Xizhang Wang, Zheng Hu. Boosting the Supercapacitance Performance of Mesostructured Carbon Nanocages by Enlarging Pore Sizes via Carbothermal Reduction^★ [J]. Acta Chimica Sinica, 2023, 81(7): 709-716.
[6]	Huang Jiapian, Liu Fei, Wu Jie. Recent Advances in the Transformation of Difluorocyclopropenes^★ [J]. Acta Chimica Sinica, 2023, 81(5): 520-532.
[7]	Jinjing Liu, Na Yang, Li Li, Zidong Wei. Theoretical Study on the Regulation of Oxygen Reduction Mechanism by Modulating the Spatial Structure of Active Sites on Platinum^★ [J]. Acta Chimica Sinica, 2023, 81(11): 1478-1485.
[8]	Shaobing Yan, Long Jiao, Chuanxin He, Hailong Jiang. Pyrolysis of ZIF-67/Graphene Composite to Co Nanoparticles Confined in N-Doped Carbon for Efficient Electrocatalytic Oxygen Reduction [J]. Acta Chimica Sinica, 2022, 80(8): 1084-1090.
[9]	Dan Wang, Bo Feng, Xiaoxin Zhang, Yanan Liu, Yan Pei, Minghua Qiao, Baoning Zong. Nitrogen-doped Carbon Pyrolyzed from ZIF-8 for Electrocatalytic Oxygen Reduction to Hydrogen Peroxide [J]. Acta Chimica Sinica, 2022, 80(6): 772-780.
[10]	Yuanhao Geng, Xiaoqiu Lin, Yaxin Sun, Huiyu Li, Yue Qin, Congju Li. Preparation of Bimetallic Conductive Metal-organic Framework Material Ni/Co-CAT for Electrocatalytic Oxygen Reduction [J]. Acta Chimica Sinica, 2022, 80(6): 748-755.
[11]	Wenjing Hu, Jiusheng Li. Synthesis of Bis/triaza Crown Ethers and Study of Their Properties as Friction Modifiers^※ [J]. Acta Chimica Sinica, 2022, 80(3): 310-316.
[12]	Zeyang Li, Yusen Yang, Min Wei. Structural Design and Performance of Electrocatalysts for Carbon Dioxide Reduction: A Review [J]. Acta Chimica Sinica, 2022, 80(2): 199-213.
[13]	Xiaohan Yu, Wei Huang, Yanguang Li. Controllable Synthesis and Photocatalytic Applications of Two-dimensional Covalent Organic Frameworks [J]. Acta Chimica Sinica, 2022, 80(11): 1494-1506.
[14]	Jinge Wang, Wei Zhou, Jiayi Li, Yani Ding, Jihui Gao. Recent Advances and Performance Enhancement Mechanisms of Pulsed Electrocatalysis [J]. Acta Chimica Sinica, 2022, 80(11): 1555-1568.
[15]	Xusheng Wang, Xu Yang, Chunhui Chen, Hongfang Li, Yuanbiao Huang, Rong Cao. Graphene Quantum Dots Supported on Fe-based Metal-Organic Frameworks for Efficient Photocatalytic CO₂ Reduction^※ [J]. Acta Chimica Sinica, 2022, 80(1): 22-28.

番荔枝皂素(4S,5S)和(4S,5R)-Muricatacin的合成及Annonacin四氢呋喃段绝对构型的确证

Synthesis of annonaceous acetogenin (4S,5S) and (4S,5R)-muricatacin as well as confirmation of absolute configuration of the tetrahydrofuran segment of annonacin

PDF

Knowledge

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments