高等学校化学学报

高等学校化学学报 ›› 1998, Vol. 19 ›› Issue (S1): 99.

• Organic Synthesis Chemistry • 上一篇    下一篇

Synthesis of Allobetulin, 28-Oxyallobetulin and Related Biomarkers from Betulin and Betulinic Acid Catalysed by Solid Acids

Jian-Xin Wang, Tong-Shuang Li, Xue-Jing Zheng   

  1. Department of Chemistry, Hebei University, Baoding 071002, Hebei Province
  • 出版日期:1998-12-31 发布日期:1998-12-31
  • 通讯作者: Tong-Shuang Li,e-mail:orgsyn@hbu.edu.cn E-mail:orgsyn@hbu.edu.cn
  • 基金资助:
    The project was supported by NSFC (29572039),Natural Science Foundation of Hebei Province and Science and Technology Commission of Hebei Province

Synthesis of Allobetulin, 28-Oxyallobetulin and Related Biomarkers from Betulin and Betulinic Acid Catalysed by Solid Acids

Jian-Xin Wang, Tong-Shuang Li, Xue-Jing Zheng   

  1. Department of Chemistry, Hebei University, Baoding 071002, Hebei Province
  • Online:1998-12-31 Published:1998-12-31
  • Contact: Tong-Shuang Li,e-mail:orgsyn@hbu.edu.cn E-mail:orgsyn@hbu.edu.cn
  • Supported by:
    The project was supported by NSFC (29572039),Natural Science Foundation of Hebei Province and Science and Technology Commission of Hebei Province

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被引次数

34

摘要： Betulin (1a) is an abundant natural product in the birch bark. Betulin itself currently has little usage. However, allobetulin (2a) has been used as an important intermediate in the further transformation of triterpenoids and as a sample for biological studies.1 For example, allobetulin was further transformed to a highly active antifeedant for heliothis zea larvae. Some biomarkers (3a,b; 4a,b) with the same or similar structure as ring-E of 2a were identified in a brown coal.3 Consequently, the conversion of 1a to synthetically, biologically and geochemically more important 2a is of great significance. The transformation of 1a to 2a was reported as early as 1922 by Schulze et al in which betulin was isomerized by formic acid, involving formation and hydrolysis of allobetulin formate, to give 2a in moderate yield.4

Abstract: Betulin (1a) is an abundant natural product in the birch bark. Betulin itself currently has little usage. However, allobetulin (2a) has been used as an important intermediate in the further transformation of triterpenoids and as a sample for biological studies.1 For example, allobetulin was further transformed to a highly active antifeedant for heliothis zea larvae. Some biomarkers (3a,b; 4a,b) with the same or similar structure as ring-E of 2a were identified in a brown coal.3 Consequently, the conversion of 1a to synthetically, biologically and geochemically more important 2a is of great significance. The transformation of 1a to 2a was reported as early as 1922 by Schulze et al in which betulin was isomerized by formic acid, involving formation and hydrolysis of allobetulin formate, to give 2a in moderate yield.4

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