【作者】 吴清来；

【导师】 覃兆海；

【作者基本信息】 中国农业大学 ， 农药学， 2004， 硕士

【摘要】 ABA是一种广泛存在于植物体内的抑制性植物激素，与植物离层形成、诱导休眠、抑制发芽、促进器官衰老和脱落、增强抗逆性等密切相关。本论文设计并完成了一条全新的外消旋脱落酸（1）全合成路线，从廉价的工业原料氧化异佛尔酮和丁炔醇出发，经过缩酮化反应、氧化反应、Wittig-Horner反应、CrSO₄选择性还原反应以及水解等七步反应实现了脱落酸的全合成，总产率达13％，与以往路线相比，该路线所用试剂廉价、合成路线简单，但产率有待提高。 为解决脱落酸2位双键在环境中易光异构化为反式结构的问题，依据电子等排体原理，将2,3-位的烯丙型的结构改变为环丙型结构，将可能解决光异构化的问题。为此，我们通过环丙烷化、亲核加成及三键选择性还原等一系列反应成功合成了ABA的2,3-环丙化类似物（88）。 所合成目标化合物及15个未见文献报道的中间体都经过了¹H和¹³CNMR、GC／MS及红外谱图的验证更多还原

【Abstract】 Abscisic acid is one of the natural plant hormone extensively distributed in higher plants and regulates many processes in plants such as the acceleration of abscission, induction of dormancy, inhibition of rooting, and stimulation of stomatal closure. In this thesis, we describe a facile and economical synthesis of (?-abscisic acid(l) from keto-isophorone and 3-butyn-2-ol through ketalization, oxidization, Witting-Horner reaction, reduction with chromium( II) sulfate and other steps in 13% total yields. Compared to the previous routes, the starting materials are more commercially available and cheaper and the synthetic process is more easily controlled in our method, but the yield of this route is still to be improved.As to isostere principle, cyclopropyl and methyl vinyl are a couple of isostere. Cis-C=C configuration on 2 position is easily isomerized to trans-form in environment according to literatures, but cycloproyl do it difficut relatively. So, replacement of 2,3- allyl unit by cyclopropyl group might give a practical method to get over the problem. For the interest of this opinion, we designed and synthesized compound (88) successfully through reactions such as cyclopropanation, nucleophilic addictions and selective reduction of triple bond etc.The structures of the target compounds and 15 intermediates have been confirmed by 1H NMR, 13C NMR, GC/MS and IR.更多还原