The first total synthesis of lamellarin α 20-sulfate, a selective inhibitor of HIV-1 integrase
The first total synthesis of lamellarin α 20-sulfate, a selective inhibitor of HIV-1 integrase
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DOI：
10.1016/j.tetlet.2006.03.121
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发表时间：
2006-05-29
影响因子：
1.8
通讯作者：
Iwao, Masatomo
中科院分区：
文献类型：
--
作者：
Yamaguchi, Tomohiro;Fukuda, Tsutomu;Iwao, Masatomo
首次合成了一种选择性HIV-1整合酶抑制剂lamellarin α 20-sulfate(1)。以hinsberg型吡咯合成和Suzuki-Miyaura偶联为关键反应，构建了13-OH和20-OH分别被异丙基和苯基不同保护的层状蛋白α核。20-硫酸酯的制备过程包括：20-OBn脱苄基化，2,2,2-三氯乙基磺化，得到20-OH脱保护13- o - pr，最后还原裂解2,2,2-三氯乙酯。(c) 2006 Elsevier Ltd.版权所有。
The first total synthesis of lamellarin alpha 20-sulfate (1), a selective inhibitor of HIV-1 integrase, has been completed. The lamellarin alpha core in which 13-OH and 20-OH were differentially protected by isopropyl and benzyl groups, respectively, was constructed by using Hinsberg-type pyrrole synthesis and Suzuki-Miyaura coupling as the key reactions. The 20-sulfate was prepared by a sequence including debenzylation of 20-OBn, 2,2,2-trichloroethylsulfation of the resulting 20-OH deprotection of 13-Oi-Pr, and final reductive cleavage of the 2,2,2-trichloroethyl ester. (c) 2006 Elsevier Ltd. All rights reserved.