Fürstner A, Mathes C, Lehmann C W
Max-Planck-Institut für Kohlenforschung, Mulheim/Ruhr, Germany.
Chemistry. 2001 Dec 17;7(24):5299-317. doi: 10.1002/1521-3765(20011217)7:24<5299::aid-chem5299>3.0.co;2-x.
Sterically hindered molybdenum(III) amido complexes of the general type [Mo[(tBu)(Ar)N]3] (1), upon treatment with CH2Cl2 or other halogen donors, have been converted into highly effective catalysts for all kinds of alkyne metathesis reactions. Although the actual nature of the propagating species formed in situ is still elusive, halogen transfer to the Mo center of 1 plays a decisive role in the activation of such precatalysts. It was possible to isolate and characterize by X-ray crystallography some of the resulting molybdenum halide derivatives such as 15, 16 and 20 which themselves were shown to be catalytically active. Numerous applications illustrate the performance of the catalytic system 1/CH2Cl2 which operates under mild conditions and tolerates an array of polar functional groups. The wide scope allows the method to be implemented into the total synthesis of sensitive and polyfunctional natural products. Most notable among them is a concise entry into the potent anticancer agents epothilone A (86) and C (88). The macrolide core of these targets is forged by ring closing alkyne metathesis (RCAM) of diyne 113, followed by Lindlar hydrogenation of cycloalkyne 114 thus formed. Since this strategy opens a stereoselective entry into (Z)-alkene 115, the approach is inherently more efficient than previous syntheses based on conventional RCM.
通式为[Mo[(tBu)(Ar)N]₃] (1)的位阻型钼(III)酰胺配合物,在与二氯甲烷或其他卤素供体反应后,已转化为用于各类炔烃复分解反应的高效催化剂。尽管原位形成的传播物种的实际性质仍不明确,但卤素向1的钼中心转移在这类预催化剂的活化中起决定性作用。通过X射线晶体学有可能分离并表征一些所得的卤化钼衍生物,如15、16和20,它们本身被证明具有催化活性。众多应用说明了催化体系1/二氯甲烷的性能,该体系在温和条件下运行,能耐受一系列极性官能团。广泛的适用范围使得该方法能够应用于敏感和多官能团天然产物的全合成。其中最值得注意的是一种简洁的合成强效抗癌药物埃坡霉素A (86)和C (88)的方法。这些目标化合物的大环内酯核心是通过二炔113的关环炔烃复分解反应(RCAM)形成的,随后对由此形成的环炔烃114进行林德拉氢化反应。由于该策略开辟了一条立体选择性合成(Z)-烯烃115的途径,该方法本质上比以前基于传统RCM的合成方法更有效。