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Oxabicyclo[3.2.1]octane Derivatives as Highly Reactive Dienophiles:  Synthesis of Bicyclo[5.n.0] Systems

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journal contribution
posted on 2005-02-03, 00:00 authored by Phillip Pelphrey, Jerry Jasinski, Ray J. Butcher, Dennis L. Wright
We have developed highly versatile, homochiral oxabicyclo[3.2.1]octadiene building blocks for the synthesis of natural products. We have found that these bridged alkenes undergo exceptionally facile Diels−Alder reactions and react faster than several well studied bicyclo[2.2.1]heptene dienophiles. The reaction proceeds with high levels of stereochemical control and in very good to excellent yields, providing access to bicyclo[5.4.0]undecane and bicyclo[5.3.0]decane systems. This reactivity is attributed to strain and homoconjugation effects.

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