Synthetic and biosynthetic methods for selective cyclisations of 4,5-epoxy alcohols to tetrahydropyrans.
Synthetic and biosynthetic methods for selective cyclisations of 4,5-epoxy alcohols to tetrahydropyrans.
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DOI：
10.1039/d1ob01905h
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发表时间：
2022-02-09
影响因子：
3.2
通讯作者：
Willis CL
中科院分区：
文献类型：
--
作者：
Bowen JI;Wang L;Crump MP;Willis CL
四氢吡喃（THPs）是天然产物和合成治疗分子中常见的结构基序。在自然界中，这些6元氧杂环通常是通过涉及氧迈克尔加成或环氧醇开环的分子内反应来组装的。事实上，聚醚天然产物由于其迷人的结构和重要的生物学特性而得到了特别广泛的研究；这些通常是通过内选择性环氧化合物打开级联形成的。本文综述了4,5-环氧醇分子内选择性开环（IERO）的合成方法及其在天然产物合成中的应用。此外，还综述了利用IERO反应合成含thp天然产物的研究进展。本文综述了4,5-环氧醇分子内选择性环氧化开环（IERO）的方法，以及利用IERO反应制备含四氢吡喃天然产物的生物合成途径。
Tetrahydropyrans (THPs) are common structural motifs found in natural products and synthetic therapeutic molecules. In Nature these 6-membered oxygen heterocycles are often assembled via intramolecular reactions involving either oxy-Michael additions or ring opening of epoxy-alcohols. Indeed, the polyether natural products have been particularly widely studied due to their fascinating structures and important biological properties; these are commonly formed via endo-selective epoxide-opening cascades. In this review we outline synthetic approaches for endo-selective intramolecular epoxide ring opening (IERO) of 4,5-epoxy-alcohols and their applications in natural product synthesis. In addition, the biosynthesis of THP-containing natural products which utilise IERO reactions are reviewed. In this review, methods for the selective intramolecular epoxide ring opening (IERO) of 4,5-epoxy-alcohols are discussed as well as biosynthetic pathways to tetrahydropyran-containing natural products which utilise IERO reactions.
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影响因子：
--
作者：
Gallimore, AR;Stark, CBW;Spencer, JB
通讯作者：
Spencer, JB
影响因子：
5.2
作者：
Furuta, Hiroki;Hasegawa, Yuki;Mori, Yuji
通讯作者：
Mori, Yuji
影响因子：
3.2
作者：
Bowen，James I.;Wang，Luoyi;Willis，Christine L.
通讯作者：
Willis，Christine L.
影响因子：
5.2
作者：
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通讯作者：
Shiina, Isamu
影响因子：
1.1
作者：
COXON, JM;HARTSHOR.MP;SWALLOW, WH
通讯作者：
SWALLOW, WH