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曲西立滨的便捷全合成

An Expedient Total Synthesis of Triciribine.

作者信息

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

机构信息

Jiangxi Key Laboratory of Organic Chemistry, Jiangxi Science & Technology Normal University, Nanchang 330013, China.

出版信息

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

DOI:10.3390/molecules22040643
PMID:28420174
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC6154533/
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--Boc-2-methylhydrazine and a trifluoroacetic acid catalyzed one-pot transformation which combined the deprotection of the -butylcarbonyl (Boc) group and ring closure reaction together to give a tricyclic nucleobase motif.

摘要

在本论文中，我们报道了三嗪核甙（一种三环7-脱氮嘌呤核苷和蛋白激酶B（AKT）抑制剂）的简便全合成方法，总产率为35%。我们的合成路线的特点是1-叔丁氧羰基-2-甲基肼的高度区域选择性取代以及三氟乙酸催化的一锅法转化反应，该反应将叔丁基羰基（Boc）基团的脱保护反应和环化反应结合在一起，生成一个三环核碱基基序。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c8d0/6154533/54a7fc139fe7/molecules-22-00643-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c8d0/6154533/5989bd535c50/molecules-22-00643-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c8d0/6154533/3196b3b5b479/molecules-22-00643-sch001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c8d0/6154533/f41513a8b9ac/molecules-22-00643-sch002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c8d0/6154533/54a7fc139fe7/molecules-22-00643-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c8d0/6154533/5989bd535c50/molecules-22-00643-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c8d0/6154533/3196b3b5b479/molecules-22-00643-sch001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c8d0/6154533/f41513a8b9ac/molecules-22-00643-sch002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c8d0/6154533/54a7fc139fe7/molecules-22-00643-g002.jpg

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