Functionalized nitroalkanes in organic synthesis. The first concise preparation of 4-hydroxyheptadecan-7-one and 14-hydroxyoctadecan-8-one, two new hydroxy ketones isolated from Chiococca alba

Abstract

The 4-hydroxyheptadecan-7-one (1) and 14-hydroxyoctadecan-8-one (2), two new hydroxyketones isolated from leaves of Chiococca alba, were synthesized, for the first time, by hydroxy-functionalized nitroalkanes 4 and 9, respectively, via two chemoselective key steps: i) nitroaldol condensation with basic alumina, and ii) direct Nef conversion of nitroalkenes to carbonyl derivatives with sodium hypophosphite, in order to preserve the OH group.