Abstract

A series of 16-arylisopimaranes has been synthesized by palladium-catalyzed arylation of the corresponding tricyclic diterpenoid isopimaric acid or its methyl ester in the presence of silver carbonate. No ligand was essential for the formation of new type optically active styrene derivatives. Good-to-excellent yields were obtained with good chemical tolerance. Silver carbonate enhanced the rate of the reaction. The use of cesium carbonate as the base requires an increase in reaction time and need for increasing amounts (2 mol%) of the palladium salt. The cross-coupling reaction proceeds with the formation of 16-arylisopimaranes with the (E)-type geometry of the double bond. Several transformations on the aryl substituent were carried out. The structure of target compounds was confirmed by X-ray diffraction study.

Graphic abstract

中文翻译：

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三环二萜的合成研究：方便地合成16-芳基异pimaranes

摘要

在碳酸银存在下，通过钯催化相应的三环二萜类异海藻酸或其甲酯的钯催化芳基化反应，合成了一系列16-芳基异pimaranes。配体对于新型光学活性苯乙烯衍生物的形成不是必需的。获得了具有良好化学耐受性的良好至优异的产率。碳酸银提高了反应速度。使用碳酸铯作为碱需要增加反应时间，并且需要增加钯盐的量（2mol％）。交叉偶联反应通过形成带有（E的16-芳基异环烷）型双键的几何形状。对芳基取代基进行了几次转化。通过X射线衍射研究确认了目标化合物的结构。

图形摘要