期刊
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
卷 130, 期 33, 页码 11114-11121出版社
AMER CHEMICAL SOC
DOI: 10.1021/ja802805c
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资金
- NIAID NIH HHS [R01 AI055475-07, R01 AI055475, R01 AI055475-06, R01 AI055475-05] Funding Source: Medline
Isolated from Hypericum species H. Chinese L. var. salicifolium, biyouyanagin A was assigned structure 1a or 1b on the basis of NMR spectroscopic analysis. This novel natural product exhibited significant anti-HIV properties and inhibition of lipopolysaccharide-induced cytokine production. Described herein are the total syntheses of biyouyanagin A and several analogues (3-11), structural revision of biyouyanagin A to 2b, and the biological properties of all synthesized compounds. The total synthesis proceeded through cascade sequences that efficiently produced enantiomerically pure key building blocks 15b (ent-zingiberene) and 18 (hyperolactone C) and featured a novel [2 + 2] photoinduced cycloaddition reaction which occurred with complete regio- and stereoselectivity. Biological investigations with the synthesized biyouyangagins A (2-11) and hyperolactones C (12-16) revealed that the activity of biyouyanagin A most likely resides in its hyperolactone C structural domain.
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