Synthetic studies on the solanacol ABC ring system by cation-initiated cascade cyclization: implications for strigolactone biosynthesis
Synthetic studies on the solanacol ABC ring system by cation-initiated cascade cyclization: implications for strigolactone biosynthesis
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DOI：
10.1039/c1ob05751k
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发表时间：
2011-01-01
影响因子：
3.2
通讯作者：
Aponick, Aaron
中科院分区：
文献类型：
--
作者：
Chojnacka, Kinga;Santoro, Stefano;Aponick, Aaron
报道了一种由简单的线性前驱体经酸催化双环化一步构建马兜铃内酯ABC环系的新方法。该反应进行了高度的立体化学控制，这可以用密度泛函计算定性地合理化。我们简明的合成方法提供了一个新的模型来思考导致这类植物激素的生物合成途径中使用的(至今)未知的化学物质。
We report a new method for constructing the ABC ring system of strigolactones, in a single step from a simple linear precursor by acid-catalyzed double cyclization. The reaction proceeds with a high degree of stereochemical control, which can be qualitatively rationalized using DFT calculations. Our concise synthetic approach offers a new model for thinking about the (as yet) unknown chemistry that is employed in the biosynthetic pathways leading to this class of plant hormones.