An Expedient Total Synthesis of Triciribine

Chen Hu; Zhizhong Ruan; Haixin Ding; Yirong Zhou; Qiang Xiao

doi:10.3390/molecules22040643

An Expedient Total Synthesis of Triciribine

Molecules. 2017 Apr 17;22(4):643. doi: 10.3390/molecules22040643.

Authors

Chen Hu¹, Zhizhong Ruan², Haixin Ding³, Yirong Zhou⁴, Qiang Xiao⁵

Affiliations

¹ Jiangxi Key Laboratory of Organic Chemistry, Jiangxi Science & Technology Normal University, Nanchang 330013, China. nchuchen@yahoo.com.
² Jiangxi Key Laboratory of Organic Chemistry, Jiangxi Science & Technology Normal University, Nanchang 330013, China. ruanzhizhong87@163.com.
³ Jiangxi Key Laboratory of Organic Chemistry, Jiangxi Science & Technology Normal University, Nanchang 330013, China. dinghaixin_2010@163.com.
⁴ Jiangxi Key Laboratory of Organic Chemistry, Jiangxi Science & Technology Normal University, Nanchang 330013, China. zyrhust@126.com.
⁵ Jiangxi Key Laboratory of Organic Chemistry, Jiangxi Science & Technology Normal University, Nanchang 330013, China. xiaoqiang@tsinghua.org.cn.

Abstract

In the present paper, we report an expedient total synthesis of triciribine, a tricyclic 7-deazapurine nucleoside and protein kinase B (AKT ) inhibitor, in 35% overall yield. Our synthesis route features a highly regioselective substitution of 1-N-Boc-2-methylhydrazine and a trifluoroacetic acid catalyzed one-pot transformation which combined the deprotection of the tert-butylcarbonyl (Boc) group and ring closure reaction together to give a tricyclic nucleobase motif.

Keywords: glycosylation; nucleosides; ring closure; total synthesis; triciribine.

MeSH terms

Chemistry Techniques, Synthetic
Models, Molecular
Molecular Structure
Nucleosides / chemical synthesis
Protein Kinase Inhibitors / chemical synthesis
Ribonucleosides / chemical synthesis*

Substances

Nucleosides
Protein Kinase Inhibitors
Ribonucleosides
triciribine