Concise total synthesis of flavone C-glycoside having potent anti-inflammatory activity

Concise total synthesis of flavone C-glycoside having potent anti-inflammatory activity
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DOI:
10.1016/j.tet.2004.08.015
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发表时间:
2004-10-11
期刊:
影响因子:
2.1
通讯作者:
Tanaka, K
Tanaka, K
中科院分区:
化学3区
文献类型:
--
作者:
Furuta, T;Kimura, T;Tanaka, K

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实现了从乌龙茶提取物中分离得到的抗炎活性黄酮C-苷的全合成。分别基于糖部分的O-C重排和连续的分子内Mitsunobu反应,将C-葡萄糖基部分引入芳基系统并构建该天然产物特有的稠合四环。这种简洁高效的合成途径适用于目标黄酮的大规模合成以及相关化合物的大型库的构建。 (C) 2004 Elsevier Ltd. 保留所有权利。
The total synthesis of anti-inflammatory active flavone C-glycoside isolated from oolong tea extract is achieved. Introducing a C-glucosyl moiety to an aryl system and constructing a fused tetracyclic ring characteristic to this natural product were conducted based on the O-to-C rearrangement of sugar moiety and the successive intramolecular Mitsunobu reaction, respectively. This concise and efficient synthetic pathway is applicable to the large-scale synthesis of target flavone and for constructing a large library of related compounds. (C) 2004 Elsevier Ltd. All rights reserved.