Application of Stereoselective Ether Transfer to the Synthesis of Isotactic Polyethers
Application of Stereoselective Ether Transfer to the Synthesis of Isotactic Polyethers
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DOI：
10.1021/jo100094d
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发表时间：
2010-06-18
影响因子：
3.6
通讯作者：
Taylor, Richard E.
中科院分区：
文献类型：
--
作者：
Liu, Kai;Arico, Joseph W.;Taylor, Richard E.
开发了一种有效、收敛的合成策略，能够合成一系列天然存在的全同立构多甲氧基化合物。醚转移后进行氢化物处理，可以在一步中同时、非对映选择性地产生两个甲氧基中心。即使在富含立体化学的多氧化体系中也能观察到高产率和非对映选择性。从甲氧基甲基醚直接生成双甲基醚部分最大限度地减少了对典型保护基策略的需求和昂贵的甲基转移试剂的使用。此外，同时生成末端伯碘化物可作为生成更高阶同系物的偶联伴侣。
An efficient, convergent synthetic strategy has been developed which enables the synthesis of a series of naturally occurring isotactic polymethoxy compound. Ether transfer followed by a hydride work up enables simultaneous, diastereoselective production of two met hoxy centers in a single step. High yields and diastereoselectivity are observed even in stereochemically rich, polyoxygenated systems. Direct generation of bis-methyl ether moieties from methoxymethyl ethers minimizes the need for typical protective group strategies and the use of expensive methyl transfer reagents. Moreover, the simultaneous generation of a terminal primary iodide serves as a coupling partner for the generation of higher order congeners.