Institut des Biomolécules Max Mousseron, IBMM, UMR CNRS 5247, Université Montpellier I, Université Montpellier II, Faculté de Pharmacie, 15, avenue Charles Flahault, France.
J Org Chem. 2010 Apr 2;75(7):2411-4. doi: 10.1021/jo1000274.
The first total synthesis of 15-D(2t)-isoprostane is described. (-)-(9S,15S)-15-D(2t)-IsoP 1 and (+)-(11R,15R)-15-epi-15-E(2t)-IsoP 2 have been obtained in 15 steps from orthogonally protected enantiopure bicycle 3. Key features include an easy introduction of the cis side chains via ozonolysis, a highly selective enzymatic chemical differentiation of a non-meso-1,5-diol, and the use of a common synthetic intermediate allowing a stereodivergent approach to the target molecules.
本文描述了 15-D(2t)-异前列腺素的首次全合成。(-)-(9S,15S)-15-D(2t)-IsoP 1 和 (+)-(11R,15R)-15-epi-15-E(2t)-IsoP 2 是从正交保护的对映纯环 3 经 15 步反应得到的。关键步骤包括通过臭氧分解容易引入顺式侧链、通过高度选择性的酶促化学差异化非内消旋 1,5-二醇以及使用共同的合成中间体，允许对目标分子进行立体发散方法。
