Synthesis of a Pladienolide B Analogue with the Fully Functionalized Core Structure
Synthesis of a Pladienolide B Analogue with the Fully Functionalized Core Structure
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DOI：
10.1021/ol201464m
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发表时间：
2011-08-05
期刊：
影响因子：
5.2
通讯作者：
Maier, Martin E.
中科院分区：
文献类型：
--
作者：
Mueller, Sarah;Mayer, Timo;Maier, Martin E.
从(R)-(-)-芳樟醇(6)开始，通过醛醇型反应，末端分化和链延伸导致酮膦酸16 （C1-C8构建基块）。在Horner-Wadsworth-Emmons反应中，16与含有邻抗me - oh构型和乙烯基碘化功能的醛22反应，得到pladienolide b的C1-C13部分。Shilna大内酯化后，烯酮26还原得到核心结构27。碘化乙烯27与三丁基苯基锡烷的Stille交叉偶联最终得到类似物30。
Starting from (R)-(-)-linalool (6), terminus differentiation and chain extension via aldol type reactions led to ketophosphonate 16 (C1-C8 building block). In a Horner-Wadsworth-Emmons reaction, 16 reacted with aldehyde 22, which contained the vicinal anti-Me-OH pattern and a vinyl iodide function, to provide the C1-C13 part of pladienolide B. After Shilna macrolactonization, reduction of the enone 26 gave the core structure 27. A Stille cross-coupling of vinyl iodide 27 with tributylphenylstannane eventually furnished analogue 30.