Alastair Couper Brodie

A novel cyclodehydration reaction of hydroxy-phenols using imidate esters as leaving groups

A mild, efficient and stereospecific intramolecular method for converting hydroxy-phenols into benzodioxans, dihydrobenzopyrans and dihydrobenzofurans via imidate esters, and suitable for large scale operation is described.

Synthesis from (–)-aristeromycin and X-ray structure of (–)-carbovir

Efficient processes are described for the synthesis of (–)-carbovir 3 and its triphosphate derivative 28 from (–)-aristeromycin 4. The X-ray structure of (–)-carbovir has been determined.

Novel cyclodehydration reaction of hydroxyphenols. An alternative to the Mitsunobu reaction

A mild, efficient and stereospecific intramolecular process for converting hydroxyphenols into benzodioxanes, dihydrobenzopyrans and dihydrobenzofurans via imidate esters is described. The only by-products are N,N-dimethylformamide and triethylamine hydrochloride which are removed by aqueous work-up making this process highly amenable to large scale operation.