浙江大学有机化学有机合成路线设计原理.pptVIP

* * （3）?-Hydroxyester * * * * （4）1,3-bicarbonyl （1,3-二羰基化合物） * * * * （5）1,4-bicarbonyl （1,4-二羰基化合物） * * （6）1,5-bicarbonyl ——迈克尔（Michael）加成反应 * * * * * * * * （7）1,6-bicarbonyl * * * * Birch还原 * * 4. Rearrangment * * 嚬哪醇重排： * * * * 习题?尝试逆合成分析并合成以下目标化合物） * * Introduction to Organic Synthesis有机合成简介 * * 合成化学家在旧的自然界旁又建起了一个新的自然界。 —— R. B. Woodward * * E. J. Corey Retrosynthetic analysis The Noble Prize in 1990 * * 1. Retrosynthetic analysis (逆合成分析) In this procedure the target molecule is transformed progressively into simpler structures by disconnecting selected carbon-carbon bonds. These disconnections rest on transforms, which are the reverse of plausible synthetic constructions. Each simpler structure, so generated, becomes the starting point for further disconnections, leading to a branched set of interrelated intermediates. A retrosynthetic transform is depicted by the = symbol, as shown in next slide. Once a complete analysis has been conducted, the desired synthesis may be carried out by application of the reactions underlying the transforms. * * Synthon Equivalent Disconnection rest on transforms * * * * Synthon （合成子) Equivalent （等价物） Polar Inversion 极性反转 * * Polar Inversion 极性反转 * * Symbol * * 策略1 Functional Group transforms （官能团转换） * * * * 策略2. Disconnection on TMs without FG （无官能团时的切断策略） —— adding FG （添加官能团） * * * * * * 策略3. Disconnection on TMs with mono FG 3.1Application of Malonic ester （丙二酸二酯，活泼亚甲基） * * * * * * 80% 99% 80% * * 酮式 烯醇式 3.2 Application of Ethyl Acetoacetate （乙酰乙酸乙酯） pKa ＝ 11 * * * * * * * * 3.3 Application of Epoxy compounds （环氧化物） * * * * * * 3.4 Disconnection on Cyclohexene （环己烯） a) D-A 反应 * * * * Birch还原 b) Birch还原 * * 4. Disconnection on Bifunctional groups （双官能团化合物） （1）?, ?-unsaturated compounds * * * * （2）?, ?-unsaturated carboxylic acid