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

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.
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Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/11581/243265
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