可扩展的区域和立体选择性合成功能化（E）-4-碘丁-3-烯-1-醇：真菌醇内酯及其衍生物的克级全合成。
Scalable Regioselective and Stereoselective Synthesis of Functionalized (E)-4-Iodobut-3-en-1-ols: Gram-Scale Total Synthesis of Fungal Decanolides and Derivatives.
机构信息
Department of Medicinal Chemistry, School of Pharmacy, The University of Kansas , Lawrence, Kansas 66047, United States.
出版信息
J Org Chem. 2018 Jan 19;83(2):980-992. doi: 10.1021/acs.joc.7b02324. Epub 2018 Jan 8.
Abstract
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.
摘要
已建立了一种可靠的方法，可分别从含有各种芳香族和脂肪族取代基的醛或环氧化物合成外消旋和手性(E)-4-碘丁-3-烯-1-醇。然后，通过提供已知的真菌醇内酯以及新型的芳香大环化合物，证明了这些化合物的用途。该方案提供了一种从(-)-aspinolide A 和(-)-5-epi-aspinolide A 获得克级规模的途径，利用催化的 Nozaki-Hiyama-Kishi 反应在最后一步中以 65-84％的收率闭合大环内酯。
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