Browsing by Author "Donohoe, Timothy J."

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Reductivealdolreactions on aromatic heterocycles

Donohoe, Timothy J.; Ace, Karl W.; Guyo, Paul M.; Helliwell, Madeleine; McKenna, Jeffrey (Elsevier, 2000-02-12)

The Birch reduction of both pyrroles and furans can be quenched with an aldehyde electrophile, thus constituting a reductivealdolreaction. Although the reaction was not stereoselective, the pyrrolines derived from reduction ...
Utility of the Ammonia-Free Birch Reduction of Electron-Deficient Pyrroles: Total Synthesis of the 20S Proteasome Inhibitor, clasto-Lactacystin b-Lactone

Donohoe, Timothy J.; Sintim, Herman O.; Sisangia, Leena; Ace, Karl W.; Guyo, Paul M.; Cowley, Andrew; Harling, John D. (Chem. Eur. J., 2005)

A new synthesis of the 20S proteasome inhibitor clasto-lactacystin b-lactone is described. Our route to this important natural product involves the partial reduction of an electron deficient pyrrole as a key step. By ...