Studies directed towards the synthesis of herbicidins. Model study based on late stage N-glycosylation

Abstract

The synthesis of nucleoside 6, via a regio- and stereoselective N-glycosylation of the undecose glycoside 4, is described. Nucleoside 6 is the first synthetic analogue of the herbicidin class of antibiotics to be reported and this model study also offers an insight into the scope and limitations associated with more general synthetic strategies based on a ‘late stage’ N-glycosylation.