69. 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

Article abstract of DOI:10.1002/hlca.19950780409

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 nitroalkanes to carbonyl derivatives with sodium hypophosphite, in order to preserve the OH group.