Department of Organic Chemistry, University of Pavia, Pavia, Italy.
J Org Chem. 2010 Dec 3;75(23):8311-4. doi: 10.1021/jo101806m. Epub 2010 Nov 9.
Endogenous nitro-fatty acids, acting as partial agonist of PPARγ, are able to lower the insulin and glucose levels without the side effects associated with common antidiabetic drugs. (E)-12-Nitrooctadec-12-enoic acid, a potent activator of this peroxisome receptor, was synthesized in a very efficient sequence via a Henry-retro-Claisen ring fragmentation, followed by a novel enzymatic cleavage of methyl esters. The latter method was then applied in the last step of the synthesis of a few labile natural products, such as prostaglandins, isoprostanes, and phytoprostanes.
内源性硝基脂肪酸，作为 PPARγ 的部分激动剂，可以降低胰岛素和血糖水平，而没有常见的抗糖尿病药物的副作用。（E）-12-硝基十八碳-12-烯酸是一种有效的过氧化物酶体受体激活剂，通过亨利-反-Claisen 环断裂反应，然后进行新颖的甲酯酶切反应，非常高效地合成了这种物质。该方法随后应用于一些不稳定天然产物（如前列腺素、异前列腺素和植物前列腺素）的最后合成步骤。
