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Practical Synthesis of (±)-Nyasol
Synthetic Communications ( IF 1.8 ) Pub Date : 2014-11-19 , DOI: 10.1080/00397911.2014.954729
Yuanying Fang , Haeil Park

Abstract A practical total synthesis of racemic nyasol (7) was explored. The α-hydroxyketo compound 3 was prepared from commercially available starting materials in two steps. Chelation-controlled reduction of the α-hydroxyketo compound 3 with Zn(BH4)2 gave the anti-1,2-diol compound 4 as the major product (anti/syn = 11.5:1). Stereospecific elimination reaction of a 1,3-cyclic thionocarbonate intermediate (5) exclusively yielded the Z-alkene compound 6. Our total synthesis is very concise (seven steps), uses commercially available starting materials, and offers good overall yield (40%). GRAPHICAL ABSTRACT

中文翻译:

(±)-Nyasol的实际合成

摘要 探索了外消旋nyasol (7) 的实用全合成。α-羟基酮化合物3由市售原料分两步制备。用 Zn(BH4)2 螯合控制的 α-羟基酮化合物 3 还原得到抗 1,2-二醇化合物 4 作为主要产物(抗/syn = 11.5:1)。1,3-环硫代碳酸酯中间体 (5) 的立体有择消除反应仅产生 Z-烯烃化合物 6。我们的全合成非常简洁(七个步骤),使用市售原料,并提供良好的总收率 (40%) . 图形概要
更新日期:2014-11-19
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