Faculty Bibliography

The concept of molecular workbenches is introduced. These workbenches are rigid templates onto which the substrate is fixed covalently and is thus arranged in a conformationally defined way. The workbench may be disconnectible (i.e, after the functionalization of the substrate it is removed by bond cleavage) or non-disconnectible. In this case the workbench is irreversibly incorporated into the target structure. This concept is illustrated by additions to (E) olefins (disconnectible workbench) and a synthesis of dihydrocodeinone (non-disconnectible workbench).

Synthetic approaches to morphine and hasubanan alkaloids involving novel reactions for the formation of their dihydrobenzofuran, piperidine and pyrrolidine ring, respectively, are described. The importance of conformational constraints for the success of these reactions is demonstrated. The syntheses of new dioxepanes, diazepanes, dithiocanes, triazenes and dioxonanes are also reported.

The synthesis of morphine alkaloids involving sigmatropic rearrangements and novel ring closures of aromatic methyl pentenyl ethers is reported.