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Chinese Journal of Organic Chemistry >

2013 , Vol. 33 >Issue 06: 1340 - 1344

DOI: https://doi.org/10.6023/cjoc201303009

Notes

Total Synthesis of Cordycepin

  • Li Qihuan ,
  • Yang Ruchun ,
  • Ruan Zhizhong ,
  • Hu Tao ,
  • Ding Haixin ,
  • Xiao Qiang
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  • Jiangxi Key Laboratory of Organic Chemistry, Jiangxi Science & Technology Normal University, Nanchang 330013

Received date: 2013-03-06

  Revised date: 2013-04-24

  Online published: 2013-05-06

Supported by

Project supported by the National Natural Science Foundation of China (NSFC, Nos.20962009, 21062006), the Program for New Century Excellent Talents in University (NCET, No.11-1000), the Training Project of Jiangxi Youth Scientists, and the Bureau of Science & Technology of Nanchang City.

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Abstract

Cordycepin has a large spectrum of biological and pharmaceutical activities, which is beneficial to human health in a number of aspects.In present paper, two total synthetic routes are developed to provide high quality product of cordycepin using D-glucose or D-xylose as the starting materials.The key step of the total synthesis is deoxygenation of 3-OH using Barton-McCombie reaction to afford 3-deoxyribose.Cordycepin is obtained in 8 steps and 7 steps with 37% and 40% overall yield, respectively.Its purity is above 98.5%.

Key words： nucleoside; total synthesis; natural product; glycosylation; radical reactions; carbohydrate

Cite this article

Li Qihuan , Yang Ruchun , Ruan Zhizhong , Hu Tao , Ding Haixin , Xiao Qiang . Total Synthesis of Cordycepin[J]. Chinese Journal of Organic Chemistry, 2013 , 33(06) : 1340 -1344 . DOI: 10.6023/cjoc201303009

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