期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 85, 期 3, 页码 1340-1351出版社
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.9b01861
关键词
-
资金
- Natural Sciences and Engineering Research Council of Canada (NSERC) [04079]
- Fonds de recherche nature et technologie Quebec for the Centre in Green Chemistry and Catalysis [FRQNT-2020-RS4-265155-CCVC]
- Universite de Montreal
- Shastri Indo-Canadian Institute, India
Sets of azabicyclo[X.Y.0]alkanone amino acids have been effectively used to identify active conformers in peptide-based drug discovery, but they usually require multiple routes to synthesize. Employing a common method from the same nine-membered unsaturated lactam precursor, we developed conditions for stereo- and regiochemical transannular cyclizations to synthesize three different indolizidin-2- and 9-one amino acid (I(2)aa and I(9)aa) analogues. For example, (3S,5R,6R,9S)- and (3S,SS,6S,9S)-I(2)aa diastereomers were prepared from hexahydro-1H-azonines by using iodine in THE and in MeCN with DIB as an additive. The regioselectivity of the transannular cyclization was influenced by amine protection to favor the synthesis of the I(9)aa isomer. Moreover, side chains were added onto the I(2)aa and I(9)aa ring systems by way of olefin intermediates that underwent Pd-catalyzed C-H bond activation and allylic oxidation.
作者
我是这篇论文的作者
点击您的名字以认领此论文并将其添加到您的个人资料中。
推荐
暂无数据