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不对称羟醛去对称化反应序列中的内酯:通往四氢-4H-呋喃并[2,3-b]吡喃-2-酮和四氢-4H-呋喃并[2,3-b]呋喃-2-酮衍生物的方法。

Lactols in an asymmetric aldol-desymmetrization sequence: access to tetrahydro-4H-furo[2,3-b]pyran-2-one and tetrahydro-4H-furo[2,3-b]furan-2-one derivatives.

作者信息

Li Ji-Yao, Yu Ke-Wei, Xie Chao-Chao, Liu Yan-Kai

机构信息

Key Laboratory of Marine Drugs, Chinese Ministry of Education, School of Medicine and Pharmacy, Ocean University of China, and Laboratory for Marine Drugs and Bioproducts of Qingdao National Laboratory for Marine Science and Technology, Qingdao 266003, People's Republic of China.

Jinan Central Hospital Affiliated to Shandong University, Jinan 250013, People's Republic of China.

出版信息

Org Biomol Chem. 2017 Feb 7;15(6):1407-1417. doi: 10.1039/c6ob02420c.

Abstract

An asymmetric aldol-desymmetrization sequence was developed which provided highly efficient access to important bicyclic oxygen-containing scaffolds with multiple chiral centers and one is a quaternary stereogenic center containing a free hydroxy group. Moreover, starting from racemic precursors, the final products were obtained as two separable diastereomers by flash chromatography. Several other heterocycles could also be easily generated with this strategy.

摘要

开发了一种不对称羟醛去对称化序列,该序列能高效合成具有多个手性中心的重要双环含氧化合物骨架,其中一个是含有游离羟基的季碳立体中心。此外,从外消旋前体出发,通过快速柱色谱法可得到两种可分离的非对映异构体形式的最终产物。利用该策略还能轻松生成其他几种杂环化合物。

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