New Approaches to the Synthesis of Pharmacologically Active Compounds From Carbohydrates

Abstract

The photobromination reaction, applied for the first time to furanose derivatives, has afforded novel 4-bromocompounds (including a nucleoside derivative). Some 3, 4-0-(α-N-amido)benzylidene compounds were encountered during the work and, form them and the 4-bromides, 4-chloro and 4-fluoro furanose derivatives have been prepared. Elimination reactions applied to the 4-bromo-compounds gave alkenes, and reactions of two of these and of related compounds with mercury(II) salts were studied, in attempts to produce functionalised cyclopentanones via α-ketomercurial intermediates. This approach to cyclopentanoids was not successful; a rationale is provided for this failure. Consequently, a route to such compounds was developed by ring contracting cyclohexanone analogues, which are readily produced by a mercury(II)-assisted carbocyclisation reaction.