比尤亚纳金A及其类似物的全合成、结构修正与生物学评价
Total synthesis, revised structure, and biological evaluation of biyouyanagin A and analogues thereof.
作者信息
Nicolaou K C, Wu T Robert, Sarlah David, Shaw David M, Rowcliffe Eric, Burton Dennis R
机构信息
Department of Chemistry, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, USA.
出版信息
J Am Chem Soc. 2008 Aug 20;130(33):11114-21. doi: 10.1021/ja802805c. Epub 2008 Jul 23.
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.
从金丝桃属植物中国金丝桃变种柳叶金丝桃中分离得到的双游岩纳金A，通过核磁共振光谱分析确定其结构为1a或1b。这种新型天然产物具有显著的抗HIV特性，并能抑制脂多糖诱导的细胞因子产生。本文描述了双游岩纳金A及其几种类似物（3 - 11）的全合成、双游岩纳金A结构修正为2b以及所有合成化合物的生物学性质。全合成通过串联反应序列高效地生成对映体纯的关键构建块15b（对映-姜烯）和18（金丝桃内酯C），并以一种具有完全区域和立体选择性的新型[2 + 2]光诱导环加成反应为特色。对合成的双游岩纳金A（2 - 11）和金丝桃内酯C（12 - 16）的生物学研究表明，双游岩纳金A的活性很可能存在于其金丝桃内酯C结构域中。
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