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
1995; Wiley; Volume: 78; Issue: 4 Linguagem: Inglês
10.1002/hlca.19950780409
ISSN1522-2675
AutoresRoberto Ballini, Giovanna Bosica, Gianni Rafaiani,
Tópico(s)Organic and Inorganic Chemical Reactions
ResumoAbstract 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.
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