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A General Strategy for the Stereocontrolled Preparation of Diverse 8-and 9-Membered Laurencia-Type Bromoethers

SA Snyder, DS Treitler, AP Brucks…

文献索引:Snyder, Scott A.; Treitler, Daniel S.; Brucks, Alexandria P.; Sattler, Wesley Journal of the American Chemical Society, 2011 , vol. 133, # 40 p. 15898 - 15901

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被引用次数: 46

摘要

A unique procedure to effect a ring-expanding bromoetherification process is described, wherein tetrahydrofurans and tetrahydropyrans are smoothly transformed into 8-and 9- membered bromoethers in a regio-and stereocontrolled manner through the use of BDSB ( bromodiethylsulfonium bromopentachloroantimonate). These products resemble the cores of the Laurencia C15 acetogenins. In light of the generality and effectiveness of the ...