Ladder Polyether Synthesis via Epoxide-Opening Cascades Directed by a Disappearing Trimethylsilyl Group
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Jamison_Ladder polyether.pdf
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Author(s)
Heffron, Timothy P.
Simpson, Graham L.
Merino, Estibaliz
Jamison, Timothy F.
Date Issued
March 2010
Journal
The Journal of Organic Chemistry
Publisher
American Chemical Society (ACS)
Citation
Heffron, Timothy P., Graham L. Simpson, Estibaliz Merino, and Timothy F. Jamison. “Ladder Polyether Synthesis via Epoxide-Opening Cascades Directed by a Disappearing Trimethylsilyl Group.” The Journal of Organic Chemistry 75, no. 8 (April 16, 2010): 2681-2701.
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Author's final manuscript
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.
MIT Department
Massachusetts Institute of Technology. Department of Chemistry
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DOI of Published Version
https://doi.org/10.1021/jo1002455
