PYRAZINE CHEMISTRY .5. SYNTHESIS OF METHYLANHYDROPICROROCCELLIN AND DIMETHYLPICROROCCELLIN
PYRAZINE CHEMISTRY .5. SYNTHESIS OF METHYLANHYDROPICROROCCELLIN AND DIMETHYLPICROROCCELLIN
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DOI：
10.1071/ch9851785
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发表时间：
1985-01-01
影响因子：
1.1
通讯作者：
ELIX, JA
中科院分区：
文献类型：
--
作者：
MARCUCCIO, SM;ELIX, JA
地衣二酮哌嗪，picroroccellin，结构已研究了几个其降解产物的合成。合成了甲基脱水小胡萝卜素（3）、（4）和（5）的三种可能的结构形式，从物理和化学性质来看，前两种化合物与天然来源的物质不同。此外，3-甲氧基哌嗪-2，5-二酮（5）的反应性完全与小红细胞素的报道一致，并且与位于哌嗪-2，5-二酮环的3-和6-位的氧官能团一致。合成了二甲基胡萝卜素（23），建立了该化合物的反式立体化学.（23）的性质与天然来源的材料所记录的性质相同。因此，我们得出结论，picrorocellin应重新表述为（2）。
The structure of the lichen diketopiperazine, picroroccellin, has been studied by the synthesis of several of its degradation products. The three possible formulations of methylanhydropicroroccellin (3), (4) and (5) were synthesized and from the physical and chemical properties, the former two compounds were shown to be dissimilar from the naturally derived material. Furthermore, the reactivity of the 3- methoxypiperazine-2,5-dione (5) entirely paralleled that reported for picroroccellin and was consistent with the oxygen functions being located at the 3- and 6-positions of the piperazine-2,5-dione ring. Dimethylpicroroccellin (23) was synthesized, so establishing the trans- stereochemistry of this compound. The properties of (23) were identical with those recorded for the naturally derived material. Hence we conclude that picroroccellin should be reformulated as (2).