Synthesis of Monoterpene Pyridine Alkaloid Aucubinine A

Chinese Journal of Organic Chemistry ›› 2004, Vol. 24 ›› Issue (11): 1429-1431. Previous Articles Next Articles

单萜吡啶生物碱 Aucubinine A 的合成

杨小宝^a,b, 花成文^*,a, 翟宏斌^*,b

^a西北大学化学系西安 710069;
^b中国科学院上海有机化学研究所现代有机合成室上海 200032

收稿日期:2003-11-03 修回日期:2004-04-19 接受日期:2004-05-27 发布日期:2022-09-21
通讯作者: ^* E-mail: huachengwen@163.com; zhaih@mail.sioc.ac.cn
基金资助:
中国科学院“百人计划”、上海市科委“科技启明星” (No. 02QB14058)、国家自然科学基金 (No. 20372073) 资助项目.

Synthesis of Monoterpene Pyridine Alkaloid Aucubinine A

YANG Xiao-Bao^a,b, HUA Cheng-Wen^*,a, ZHAI Hong-Bin^*,b

^aDepartment of Chemistry, Northwest University, Xi'an 710069, China;
^bShanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 20003, China

Received:2003-11-03 Revised:2004-04-19 Accepted:2004-05-27 Published:2022-09-21

Abstract

Aucubinine A, a monoterpene alkaloidisolated from the metabolites of aucubin in the presence of human intestinal bacteria, has been synthesized from 4-hydro-5-hydroxyl-3-methylidene-5H-cyclopentadieno[2,1-c]pyridine (6) in 30% overall yield. Hydroboration followed by oxidation in basic medium converted 6 todiastereomeric diols 7, which were subjected to selective benzylic oxidation to form aucubinine A.

Key words: aucubinine A, cyclopentadieno[2,1-c]pyridine, monoterpene alkaloid, synthesis

Cite this article

YANG Xiao-Bao, HUA Cheng-Wen, ZHAI Hong-Bin. Synthesis of Monoterpene Pyridine Alkaloid Aucubinine A[J]. Chinese Journal of Organic Chemistry, 2004, 24(11): 1429-1431.

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单萜吡啶生物碱 Aucubinine A 的合成

Synthesis of Monoterpene Pyridine Alkaloid Aucubinine A

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