2H-Pyran-2-ones from Trichoderma viride and Trichoderma asperellum
2H-Pyran-2-ones from Trichoderma viride and Trichoderma asperellum
复制标题
来自绿色木霉和黑霉木霉的 2H-吡喃-2-酮
DOI：
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发表时间：
2013
期刊：
影响因子：
--
通讯作者：
Jeroen S. Dickschat
中科院分区：
文献类型：
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作者：
Susanne M. Wickel;Christian A. Citron;Jeroen S. Dickschat
采用闭环溶出分析（CLSA）顶空技术收集土壤真菌绿色木霉272和黑曲霉328释放的挥发物，并通过GC/MS对获得的提取物进行分析。几种烷基和烯基-2H-吡喃-2-酮，包括已知化合物6-戊基-2H-吡喃-2-酮和(E)-6-(戊-1-烯-1-基)-2H-吡喃-2-酮，以及新衍生物(E)-6-(戊-2-烯-1-基)-2H-吡喃-2-酮、6-丙基-2H-吡喃-2-酮，和 发现6-庚基-2H-吡喃-2-酮。还检测到了烯基衍生物 (E)-6-(hept-1-en-1-yl)-2H-pyran-2-one，之前通过 MS 分析从海洋灰霉病中初步鉴定出该衍生物。所有烯基吡喃酮都是通过使用报道的Stille偶联然后内酯化合成的，而烷基化吡喃酮是通过报道的5-烷基戊-2-en-5-内酯的自由基溴化和脱溴化氢的合成方法获得的。由于这两种情况的产率均不令人满意，并且与报道的类似化合物的产率相差甚远，因此使用 Schreiber 及其同事最近开发的末端炔烃与丙炔酸的金催化偶联再次合成了所有化合物，在所有情况下均获得了高产率。给出了合成方法的比较。
Volatiles emitted by the soil fungi Trichoderma viride 272 and Trichoderma asperellum 328 were collected by using the closed loop stripping analysis (CLSA) headspace technique, and the obtained extracts were analysed by GC/MS. Several alkyl- and alkenyl-2H-pyran-2-ones, including known compounds 6-pentyl-2H-pyran-2-one and (E)-6-(pent-1-en-1-yl)-2H-pyran-2-one, and the new derivatives (E)-6-(pent-2-en-1-yl)-2H-pyran-2-one, 6-propyl-2H-pyran-2-one, and 6-heptyl-2H-pyran-2-one were found. The alkenyl derivative (E)-6-(hept-1-en-1-yl)-2H-pyran-2-one, previously tentatively identified from a marine Botrytis by MS analysis, was also detected. All alkenyl pyrones were synthesised by using a reported Stille coupling followed by lactonisation, whereas the alkylated pyrones were obtained through a reported synthetic approach by radical bromination of 5-alkylpent-2-en-5-olides and dehydrobromination. Because the yields in both cases were not satisfactory and fell a long way short of the yields reported for similar compounds, all compounds were synthesised again using a gold-catalysed coupling of terminal alkynes with propiolic acid recently developed by Schreiber and co-workers, giving high yields in all cases. A comparison of the synthetic methods is given.
影响因子：
5.1
作者：
Garo, E;Starks, CM;Clardy, J
通讯作者：
Clardy, J