1-Nitroicosane as the Key Building Block for the First Synthesis of Triacontan-11-ol, A New Fatty Alcohol Isolated from Argemone mexicana

Roberto Ballini; Dennis Fiorini; Alessandro Palmieri

doi:10.1055/s-2005-872216

SHORTPAPER

1-Nitroicosane as the Key Building Block for the First Synthesis of Triacontan-11-ol, A New Fatty Alcohol Isolated from Argemone mexicana

Roberto Ballini*, Dennis Fiorini, Alessandro Palmieri
Dipartimento di Scienze Chimiche, Università, via S. Agostino 1, 62032 Camerino, Italy
Fax: +39(0737)402297; e-Mail: roberto.ballini@unicam.it;

Abstract

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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.

Key words

triacontan-11-ol - nitroalkanes - Nef reaction - natural products - nitroalkenes

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