期刊
TETRAHEDRON
卷 69, 期 51, 页码 10946-10954出版社
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2013.10.057
关键词
Amination; Cascade reaction; Copper; One-pot; PDE
资金
- Cabinet Office, Government of Japan through its 'Funding Program for Next Generation World-Leading Researchers' [LS008]
- Ministry of Education, Culture, Sports, Science, and Technology, Japan
- KAKENHI [20390003]
A concise total synthesis of PDE-I and -II featuring copper-mediated double aryl amination with the combination of Cul, CsOAc, and Cs2CO3 is described. The highly substituted pyrroloindole skeleton was constructed by a one-pot five-step sequence including double aryl amination,)beta-elimination, deprotection of a Cbz group, and unexpected formation of an indole via removal of an Ns group followed by rearomatization. The undesired elimination of the protecting group (Ns group) was hampered by using the Boc group as a protecting group in the second-generation synthesis, which excluded the reduction of the indole required in the first-generation synthesis. (C) 2013 Elsevier Ltd. All rights reserved.
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