Hm. Binch et al., CARBOHYDRATE BUILDING-BLOCKS IN HETEROCYCLIC CHEMISTRY - SYNTHETIC STUDIES DIRECTED TOWARDS THE HERBICIDINS, Pure and applied chemistry, 68(3), 1996, pp. 589-592
Recent synthetic studies directed towards the herbicidin class of nucl
eosides are described Aldehyde 7, incorporating the requisite adenine
unit, has been prepared but failed to undergo base-induced aldol react
ions with ketone 3. This problem was overcome using the cerium enolate
corresponding to 3, which is generated from alpha-bromoketone 9. Reac
tion of this species with aldehyde 7 leads to the enone 8.