The isolation and synthesis of polyandrocarpamines A and B.: Two new 2-aminoimidazolone compounds from the Fijian ascidian, Polyandrocarpa sp.
The isolation and synthesis of polyandrocarpamines A and B.: Two new 2-aminoimidazolone compounds from the Fijian ascidian, Polyandrocarpa sp.
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DOI：
10.1016/s0040-4020(02)00228-4
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发表时间：
2002-04-15
期刊：
影响因子：
2.1
通讯作者：
Ireland, CM
中科院分区：
文献类型：
--
作者：
Davis, RA;Aalbersberg, W;Ireland, CM
斐济海鞘的化学成分研究结果分离出两个新的2-氨基咪唑酮衍生物，聚雄果芸香胺A（1）和B（2）。这些独特的代谢产物的结构通过光谱数据的解释和全合成来确定。使用羟醛缩合化学完成I的立体特异性合成，以产生亚芳基硫代乙内酰脲，其随后转胺以产生聚雄果芸香胺A。合成物I的脱甲基化得到聚雄酮香豆素B。天然产物和合成的聚雄果胺都基于C-13/H-1长程偶合常数（使用gHSQMBC实验测量）被指定为关于环外双键（C-5/C-7）的Z几何构型。(C)2002爱思唯尔科技有限公司版权所有。
Chemical investigation of a Fijian ascidian, Polyandrocarpa sp., has resulted in the isolation of two new 2-aminoimidazolone-derived compounds, polyandrocarpamines A (1) and B (2). The structures of these unique metabolites were determined by the interpretation of spectroscopic data and cominned by total synthesis. The stereospecific synthesis of I was accomplished using aldol condensation chemistry to generate an arylidene thiohydantoin that was subsequently transaminated to yield polyandrocarpamine A. Demethylation of synthetic I afforded polyandrocarparnme B. Both the natural product and synthetic: polyandrocarpamines were assigned Z geometries about the exocyclic double bond (C-5/C-7) on the basis of C-13/H-1 long-range coupling constants, which were measured using a gHSQMBC experiment. (C) 2002 Elsevier Science Ltd. All rights reserved.