从联萘酚四醇到四溴二苯醚的海洋代谢产物的结构重分配。
Structural reassignment of a marine metabolite from a binaphthalenetetrol to a tetrabrominated diphenyl ether.
机构信息
Roy and Diana Vagelos Laboratories, Department of Chemistry, University of Pennsylvania, Philadelphia, Pennsylvania 19104-6323, USA.
出版信息
J Nat Prod. 2012 Jun 22;75(6):1125-9. doi: 10.1021/np300141t. Epub 2012 Jun 12.
Abstract
The structure of a reported natural product isolate has been revised from (S)-2,2'-dimethoxy-[1,1'-binaphthalene]-5,5',6,6'-tetraol to a known tetrabrominated diphenyl ether. After total synthesis of the reported binaphthalenetetrol was accomplished via a key reduction of a binaphtho-ortho-quinone, comparison of the physical properties and NMR spectroscopic data of the synthetic material indicated that the structure of the natural product isolate was incorrect. Evaluation of the authentic natural product suggested the structure is a tetrabrominated diphenyl ether, likely 3,5-dibromo-2-(3,5-dibromo-2-methoxyphenoxy)phenol.
摘要
所报道的天然产物分离物的结构已从（S）-2,2'-二甲氧基-[1,1'-联萘]-5,5',6,6'-四醇修订为已知的四溴化二苯醚。通过联萘-邻醌的关键还原完成了所报道的联萘四醇的全合成后，比较合成材料的物理性质和 NMR 光谱数据表明，天然产物分离物的结构不正确。对真实天然产物的评估表明，其结构为四溴化二苯醚，可能为 3,5-二溴-2-（3,5-二溴-2-甲氧基苯氧基）苯酚。
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