Ladder Polyether Synthesis via Epoxide-Opening Cascades Directed by a Disappearing Trimethylsilyl Group

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• 作者：Timothy P. Heffron ; Graham L. Simpson ; Estibaliz Merino ; Timothy F. Jamison
• 刊名：Journal of Organic Chemistry
• 出版年：2010
• 出版时间：April 16, 2010
• 年：2010
• 卷：75
• 期：8
• 页码：2681-2701
• 全文大小：1597K
• 年卷期：v.75,no.8(April 16, 2010)
• ISSN：1520-6904

文摘

Epoxide-opening cascades offer the potential to construct complex polyether natural products expeditiously and in a manner that emulates the biogenesis proposed for these compounds. Herein we provide a full account of our development of a strategy that addresses several important challenges of such cascades. The centerpiece of the method is a trimethylsilyl (SiMe₃) group that serves several purposes and leaves no trace of itself by the time the cascade has come to an end. The main function of the SiMe₃ group is to dictate the regioselectivity of epoxide opening. This strategy is the only general method of effecting endo-selective cascades under basic conditions.