10.1021/ol047725i.s003 Phillip Pelphrey Phillip Pelphrey Jerry Jasinski Jerry Jasinski Ray J. Butcher Ray J. Butcher Dennis L. Wright Dennis L. Wright Oxabicyclo[3.2.1]octane Derivatives as Highly Reactive Dienophiles:  Synthesis of Bicyclo[5.<i>n</i>.0] Systems American Chemical Society 2005 bicyclo bridged alkenes reaction proceeds homoconjugation effects stereochemical control 2005-02-03 00:00:00 Journal contribution https://acs.figshare.com/articles/journal_contribution/Oxabicyclo_3_2_1_octane_Derivatives_as_Highly_Reactive_Dienophiles_Synthesis_of_Bicyclo_5_i_n_i_0_Systems/3302518 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.