期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 83, 期 13, 页码 7290-7295出版社
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.8b00039
关键词
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资金
- JSPS KAKENHI [16H05077, 16K18848]
- Basis for Supporting Innovative Drug Discovering and Life Science Research (BINDS) from AMED
- Grants-in-Aid for Scientific Research [16K18848, 16H05077] Funding Source: KAKEN
We describe a concise enantioselective synthesis of the HIV-protease inhibitor nelfinavir (1) via a new route in which the key step is construction of the central optically active 1,2-amino alcohol framework via asymmetric bromocyclization of bisallylic amide with N-bromosuccinimide in the presence of a catalytic amount of (S)-BINAP or (S)-BINAP monoxide. The remaining alkene and bromo functionalities were used to install the requisite thioether and chiral perhydroisoquinoline units, respectively.
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