期刊
TETRAHEDRON LETTERS
卷 55, 期 39, 页码 5390-5393出版社
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2014.08.020
关键词
Molecular scaffolds; 1-Azaadamantanes; Vicinal amino alcohols; Aza-Prins reaction; Olefin epoxidation; Epoxide opening
资金
- Australian Research Council [DP130102400]
The vast majority of scaffolds found in natural products are absent from the currently available compound collections for biological screening. At the same time, scaffolds derived from natural products may have a distinct advantage over non-natural cores in terms of providing compounds endowed with biological activities and should be used extensively in screening library design. We have developed a synthetic approach to merging a naturally occurring 1-azaadamantane core with a vicinal amino alcohol moiety that is also common in natural product chemical space. The synthesis features diastereoselective epoxidation of racemic chiral 2,6-diaryl-4-methylene 1-azaadamantanes with subsequent S(N)2-type epoxide opening in aqueous isopropanol. (C) 2014 Elsevier Ltd. All rights reserved.
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