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Scalable Regioselective and Stereoselective Synthesis of Functionalized (E)-4-Iodobut-3-en-1-ols: Gram-Scale Total Synthesis of Fungal Decanolides and Derivatives
The Journal of Organic Chemistry ( IF 3.6 ) Pub Date : 2018-01-08 00:00:00 , DOI: 10.1021/acs.joc.7b02324
Alexander M. Sherwood 1 , Samuel E. Williamson 1 , Stephanie N. Johnson 1 , Anil Yilmaz 1 , Victor W. Day 1 , Thomas E. Prisinzano 1
Affiliation  

A reliable protocol to synthesize both racemic and chiral (E)-4-iodobut-3-en-1-ols from aldehydes or epoxides, respectively, containing various aromatic and aliphatic substitutions has been established. The utility of these compounds was then demonstrated by providing access to known fungal decanolides as well as novel aromatic macrocycles. The protocol provided a gram-scale route to (−)-aspinolide A and (−)-5-epi-aspinolide A utilizing a catalytic Nozaki–Hiyama–Kishi reaction to close the macrolide in the final step in 65–84% yields.

中文翻译:

功能化的(E)-4-碘代丁-3-en-1-ols的可扩展的区域选择性和立体选择性合成:真菌癸醇化物和衍生物的克级总合成。

建立了分别从醛或环氧化物分别包含各种芳族和脂族取代基合成外消旋和手性(E)-4-碘丁-3--3-烯-1-醇的可靠方案。然后,通过提供对已知真菌癸醇化物以及新型芳香族大环化合物的使用,证明了这些化合物的效用。该协议利用催化的Nozaki-Hiyama-Kishi反应在最后一步以65-84%的产率封闭大环内酯,从而为(-)-aspinolide A和(-)-5- epi -aspinolide A提供了克级的途径。
更新日期:2018-01-08
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