The first synthesis of triacontan-11-ol, a new fatty alcohol isolated from Argemone mexicana, has been realized starting from the nitroaldol reaction of 1-nitroicosane with decanal. Dehydration of the obtained nitroalkanol gives a long-chain nitroalkene which is then reduced to the corresponding nitroalkane. Nef transformation of the latter produces a ketone that is easily reduced to the fatty alcohol 9 in 21% overall yield.
1-Nitroicosane as the Key Building Block for the First Synthesis of Triacontan-11-ol, A New Fatty Alcohol Isolated from Argemone mexicana
BALLINI, Roberto;FIORINI, Dennis;PALMIERI, Alessandro
2005-01-01
Abstract
The first synthesis of triacontan-11-ol, a new fatty alcohol isolated from Argemone mexicana, has been realized starting from the nitroaldol reaction of 1-nitroicosane with decanal. Dehydration of the obtained nitroalkanol gives a long-chain nitroalkene which is then reduced to the corresponding nitroalkane. Nef transformation of the latter produces a ketone that is easily reduced to the fatty alcohol 9 in 21% overall yield.File in questo prodotto:
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