1. Ladder Polyether Synthesis via Epoxide-Opening Cascades Directed by a Disappearing Trimethylsilyl Group
- Author
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Massachusetts Institute of Technology. Department of Chemistry, Heffron, Timothy P., Simpson, Graham L., Merino, Estibaliz, Jamison, Timothy F., Massachusetts Institute of Technology. Department of Chemistry, Heffron, Timothy P., Simpson, Graham L., Merino, Estibaliz, and Jamison, Timothy F.
- Abstract
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 (SiMe[subscript 3]) 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 SiMe[subscript 3] group is to dictate the regioselectivity of epoxide opening. This strategy is the only general method of effecting endo-selective cascades under basic conditions., Johnson & Johnson (Fellowship), Boehringer Ingelheim Pharmaceuticals (Fellowship), US-UK Fulbright Commission
- Published
- 2013