Dihydropyrans are common synthetic targets due to their diverse biological activity and the vast number of naturally occurring compounds in which they are found.  This status has led to the development of a number of synthetic routes, but each encounters limitations in either scope or efficiency.  Our development of a new method seeks to avoid these limitations in order to improve access to these important heterocycles.  We describe the use of a simple reagent, 1,3-bis(trimethylsilyl)propene, designed to undergo a tandem Sakurai/silyl-Prins reaction to produce dihydropyran rings in a single reaction step.  Subsequent reaction of the endocyclic double bond can provide routes to tetrahydropyrans or heterocyclic diols leading to more classes of natural products.  Early results using simple compounds are promising, but further work needs to explore the use of this reagent in the formation of a diverse range of oxygen heterocycles to demonstrate broad applicability.

Rapid construction of dihydropyrans via a tandem Sakurai/silyl-Prins reaction sequence

244th National Meeting (2012)

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