In this paper are presented the results of the preliminary studies conducted on two model substrates that allowed the testing of various strategies and set the proper conditions that thereafter culminated in the synthesis of the C1–C23 chain of enacyloxin-IIa and its congeners. Innovative strategic options were explored on each model allowing the stereochemical control of the following two elements: (a) the 2E, 4E, 6E, 8E, and 10Z chlorinated undecapentaenoic chain, thanks to Z-selective Kaneda’s alkyne allylchlorination and an E-selective Pd/Cu allene–alkyne coupling and (b) the unusual syn-anti −OH/–Cl/–OCONH₂ C17–C19 triad, thanks to a highly diastereoselective Mukaiyama aldol reaction.

中文翻译：

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利用模型优化恩昔洛辛系列氯化链特征的合成策略

本文介绍了对两种模型底物进行的初步研究的结果，这些模型底物允许测试各种策略并设置适当的条件，最终合成 enacyloxin-IIa 及其同系物的 C1-C23 链。每个模型都探索了创新的战略选择，允许对以下两个元素进行立体化学控制：(a) 2 E、4 E、6 E、8 E和 10 Z氯化十一碳烯链，这要归功于Z选择性 Kaneda 的炔烯丙基氯化和E-选择性Pd/Cu 丙二烯-炔偶联和 (b) 不寻常的顺式-抗-OH /–Cl/–OCONH ₂ C 17– C 19 三联体，这要归功于高度非对映选择性的 Mukaiyama 羟醛反应。