期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 76, 期 10, 页码 4154-4157出版社
AMER CHEMICAL SOC
DOI: 10.1021/jo2004132
关键词
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资金
- Academia Sinica
- National Science Council, Taiwan, Republic of China
The first enantioselective total synthesis of (+)-(R)-concentricolide, the enantiomer of an anti-HIV-1 agent isolated from Daldinia concentrica, from 2-iodophenol in 7 steps reveals the (S)-configuration for the natural form of the furanophthalide. The key features include an anionic ortho-Fries rearrangement to furnish 3-iodosalicylamide, facile construction of the benzofuran system employing the tandem Sonogashira coupling annulation reaction, directed ortho metalation to introduce a propanoyl group, as well as CBS reduction, establishing the stereocenter enantioselectively.
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