Efficient Synthesis of 2-Ethyl-A-ring Analogues of 19-Nor-1α,25-dihydroxy Vitamin D3

Chemical Research in Chinese Universities ›› 2003, Vol. 19 ›› Issue (2): 165-173.

• Articles • Previous Articles Next Articles

Efficient Synthesis of 2-Ethyl-A-ring Analogues of 19-Nor-1α,25-dihydroxy Vitamin D₃

WANG Qiuan¹, ZHAO Yu-rui²

1. College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082, P. R. China;
2. Department of Organic Chemistry, University of Gent, Krijgslaan 281 S4, B-9000 Gent, Belgium

Received:2002-04-02 Online:2003-04-24 Published:2011-08-06

Abstract

Abstract: The novel 19-nor-lα,25-dihydroxy vitamin D3 analogues possessing an ethyl at the 2-position(4 and 5), were synthesized by coupling 25-hydroxy Windaus-Grundmann ketone derivative 20 with A-ring synthons(15 and 19) respectively. The enantioselective synthesis of substituted bicyclic[3,1,0] hexanes structure A-ring synthons, started from all-cis-3,5-dihydroxy-4-ethyl-1-(methoxycarbonyl)cyclohexane via lipase-catalyzd asymmetrization, was demonstrated.

Key words: 2-Ethyl-19-nor-1α,25-dihydroxy vitamin D₃, Synthesis, Lipase-catalyzed, Asymmetrization

WANG Qiuan, ZHAO Yu-rui. Efficient Synthesis of 2-Ethyl-A-ring Analogues of 19-Nor-1α,25-dihydroxy Vitamin D₃[J]. Chemical Research in Chinese Universities, 2003, 19(2): 165-173.

[1]	FAN Kui, SUN Yining, XU Pengcheng, GUO Jian, LI Zhenhua, SHAO Mingfei. Single-atom Catalysts Based on Layered Double Hydroxides [J]. Chemical Research in Chinese Universities, 2022, 38(5): 1185-1196.
[2]	JI Yuancheng, XU Jiayun, SUN Hongcheng, and LIU Junqiu. Artificial Photosynthesis(AP): from Molecular Catalysts to Heterogeneous Materials [J]. Chemical Research in Chinese Universities, 2022, 38(3): 688-697.
[3]	CHEN Juan, WANG Jiajia, CHEN Chongan and YANG Guoyu. Two New Borates Built by Different Types of {B₉} Cluster Units [J]. Chemical Research in Chinese Universities, 2022, 38(3): 744-749.
[4]	Mohammad Javad TAGHIZADEH, Maryam Saleh MOHAMMADNIA, Masoumeh GHALKHANI, Esmail SOHOULI. Improved Method for the Total Synthesis of Azaperone and Investigation of Its Electrochemical Behavior in Aqueous Solution [J]. Chemical Research in Chinese Universities, 2022, 38(2): 546-551.
[5]	SUN Xiao-Shuang, QIN Dan, LI Xu-Yan, YANG Guo-Yu. A New Tubular Borate Built by[B₁₄O₂₄(OH) ₆]^12- Cluster Units [J]. Chemical Research in Chinese Universities, 2022, 38(1): 123-127.
[6]	WANG Zelin, LIU Guihao, SHEN Tianyang, TAN Ling, ZHAO Yufei, SONG Yu-Fei. Remote Synthesis of Layered Double Hydroxide Nanosheets Through the Automatic Chemical Robot [J]. Chemical Research in Chinese Universities, 2022, 38(1): 217-222.
[7]	ZHANG Xiaosi, YANG Miao, TIAN Peng, LIU Zhongmin. Progress in Seed-assisted Synthesis of (Silico) Aluminophosphate Molecular Sieves [J]. Chemical Research in Chinese Universities, 2022, 38(1): 1-8.
[8]	LUAN Huimin, WU Qinming, ZHANG Jian, WANG Yeqing, MENG Xiangju, XIAO Feng-Shou. Sustainable Synthesis of Core-Shell Structured ZSM-5@Silicalite-1 Zeolite [J]. Chemical Research in Chinese Universities, 2022, 38(1): 136-140.
[9]	FANG Yuan, HEYDARI Zahra, LIU Chenghao, ZHANG Nianyue, CUCCIA Louis A., IVASENKO Oleksandr, PEREPICHKA Dmitrii F.. Glaser Coupling of Substituted Anthracene Diynes on a Non-metallic Surface at the Vapor-Solid Interface [J]. Chemical Research in Chinese Universities, 2021, 37(5): 1143-1148.
[10]	ZHAO Lei, YANG Ge, GUO Hailing, WANG Chunzheng, WANG Lijuan, Svetlana MINTOVA. Effect of Sodium Concentration on the Synthesis of Faujasite by Two-step Synthesis Procedure [J]. Chemical Research in Chinese Universities, 2021, 37(5): 1137-1142.
[11]	ZHANG Ling, FU Yihong, DING Yue, MENG Jiao, WANG Zhenchao, WANG Peiyi. Antibacterial Activity of Novel 18β-Glycyrrhetinic Hydrazide or Amide Derivatives [J]. Chemical Research in Chinese Universities, 2021, 37(3): 662-667.
[12]	DONG Xin, CHEN Xi, ZHOU Zhaohui. Efficient Synthesis of p-Hydroxyphenyl Ethanol from Hydrogenation of Methyl p-Hydroxyphenylacetate with CNTs-promoted Cu-Zr Catalyst [J]. Chemical Research in Chinese Universities, 2021, 37(3): 745-750.
[13]	LI Yuan, LI Ruizhe, LI Zhenhua, WEI Weiqin, OUYANG Shuxin, YUAN Hong, ZHANG Tierui. Effect of Support on Catalytic Performance of Photothermal Fischer-Tropsch Synthesis to Produce Lower Olefins over Fe₅C₂-based Catalysts [J]. Chemical Research in Chinese Universities, 2020, 36(6): 1006-1012.
[14]	ZHAO Yanhui, YU Haifeng, LIAO Peiqiu, WANG Wenju. Green and Efficient Synthesis of 3-Pyrazolyl Indoles in Water [J]. Chemical Research in Chinese Universities, 2020, 36(5): 847-852.
[15]	ZHANG Baochang, LI Yulei, SHI Weiwei, WANG Tongyue, ZHANG Feng, LIU Lei. Chemical Synthesis of Proteins Containing 300 Amino Acids [J]. Chemical Research in Chinese Universities, 2020, 36(5): 733-747.

Efficient Synthesis of 2-Ethyl-A-ring Analogues of 19-Nor-1α,25-dihydroxy Vitamin D₃

PDF (PC)

Knowledge

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments