Oxabicyclo[3.2.1]octane derivatives as highly reactive dienophiles: synthesis of bicyclo[5.n.0] systems

Phillip Pelphrey; Jerry Jasinski; Ray J Butcher; Dennis L Wright

doi:10.1021/ol047725i

Oxabicyclo[3.2.1]octane derivatives as highly reactive dienophiles: synthesis of bicyclo[5.n.0] systems

Org Lett. 2005 Feb 3;7(3):423-5. doi: 10.1021/ol047725i.

Authors

Phillip Pelphrey¹, Jerry Jasinski, Ray J Butcher, Dennis L Wright

Affiliation

¹ Burke Laboratories, Department of Chemistry, Dartmouth College, Hanover, NH 03755, USA.

PMID: 15673255
DOI: 10.1021/ol047725i

Abstract

[reaction: see text] 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.