Epoxide-Based Synthetic Approaches toward Polypropionates and Related Bioactive Natural Products.
Epoxide-Based Synthetic Approaches toward Polypropionates and Related Bioactive Natural Products.
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DOI：
10.3390/ijms24076195
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发表时间：
2023-03-24
影响因子：
5.6
通讯作者：
Bugarin, Alejandro
中科院分区：
文献类型：
--
作者：
Rodriguez-Berrios, Raul R.;Isbel, Stephen R.;Bugarin, Alejandro
聚丙酸酯单元是聚酮化合物中许多天然产物的常见结构特征，其中一些已显示出广泛的抗菌和治疗潜力。聚丙酸酯由具有特定构型的甲基和羟基交替的碳骨架组成。已经开发了多种合成聚丙酸酯的方法，在此我们首次涵盖了多年来由多个研究小组（如Kishi、Katsuki、Marashall、Miyashita、Prieto、Sarabia、Jung、McDonald等）报道的所有基于环氧化物的方法。本综述描述并总结了几种以环氧化物为关键中间体的聚丙酸酯片段和天然产物的合成。这些合成方法包括环氧化物（环氧醇、环氧酰胺和环氧酯）的对映选择性和非对映选择性合成，以及它们与碳和/或氢化物亲核试剂的区域选择性裂解。此外，我们还描述了使用基于环氧化物的方法合成的聚丙酸酯及相关天然产物的分离和生物活性。总之，基于环氧化物的方法是构建聚丙酸酯的一种非羟醛替代方法。
Polypropionate units are a common structural feature of many of the natural products in polyketides, some of which have shown a broad range of antimicrobial and therapeutic potential. Polypropionates are composed of a carbon skeleton with alternating methyl and hydroxy groups with a specific configuration. Different approaches have been developed for the synthesis of polypropionates and herein we include, for the first time, all of the epoxide-based methodologies that have been reported over the years by several research groups such as Kishi, Katsuki, Marashall, Miyashita, Prieto, Sarabia, Jung, McDonald, etc. Several syntheses of polypropionate fragments and natural products that employed epoxides as key intermediates have been described and summarized in this review. These synthetic approaches involve enatio- and diastereoselective synthesis of epoxides (epoxy-alcohols, epoxy-amides, and epoxy-esters) and their regioselective cleavage with carbon and/or hydride nucleophiles. In addition, we included a description of the isolation and biological activities of the polypropionates and related natural products that have been synthetized using epoxide-based approaches. In conclusion, the epoxide-based methodologies are a non-aldol alternative approach for the construction of polypropionate.
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影响因子：
2.1
作者：
Rodríguez-Berríos RR;Torres G;Prieto JA
通讯作者：
Prieto JA
影响因子：
16.6
作者：
Van Dyke, Aaron R.;Jamison, Timothy F.
通讯作者：
Jamison, Timothy F.
DOI：
10.1021/jo3008226
发表时间：
2013-01-04
期刊：
The Journal of organic chemistry
影响因子：
--
作者：
Chen M;Roush WR
通讯作者：
Roush WR
影响因子：
2.1
作者：
Ciavatta, ML;Gavagnin, M;Mattia, CA
通讯作者：
Mattia, CA
影响因子：
15
作者：
Burova, SA;McDonald, FE
通讯作者：
McDonald, FE