Martín-Rodríguez María, Galán-Fernández Raquel, Marcos-Escribano Andrés, Bermejo Francisco A
Departamento de Química Orgánica, Universidad de Salamanca, 37008 Salamanca, Spain.
J Org Chem. 2009 Feb 20;74(4):1798-801. doi: 10.1021/jo8026033.
The total synthesis of (+)-paeonisuffrone starting from (+)-10-hydroxycarvone is described. The key step of our synthetic strategy is a titanium-catalyzed stereoselective cyclization initiated by epoxide opening through electron transfer. This reaction stereoselectively affords the highly oxygenated pinane skeleton present in the target molecule and opens a new and effective approach to the synthesis of the complex, biologically active terpenoids isolated from the roots of the Chinese paeony (Paeonia albiflora Pallas and Paeonia suffruticosa Andrews).
描述了从(+)-10-羟基香芹酮出发全合成(+)-芍药二酮的过程。我们合成策略的关键步骤是通过电子转移引发的环氧化物开环的钛催化立体选择性环化反应。该反应立体选择性地得到目标分子中存在的高度氧化的蒎烷骨架，并为从中国芍药（芍药和牡丹）根中分离出的复杂生物活性萜类化合物的合成开辟了一条新的有效途径。
