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Ladder polyether synthesis via epoxide-opening cascades directed by a disappearing trimethylsilyl group.

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(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(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.

SUBMITTER: Heffron TP

PROVIDER: S-EPMC3018858 | biostudies-literature | 2010 Apr

REPOSITORIES: biostudies-literature

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Ladder polyether synthesis via epoxide-opening cascades directed by a disappearing trimethylsilyl group.

Heffron Timothy P TP Simpson Graham L GL Merino Estibaliz E Jamison Timothy F TF

The Journal of organic chemistry 20100401 8

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(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 ...[more]

PMID: 20302314

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