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An efficient route to the musk odorant (R,Z)-5-muscenone via base-metal-catalysis

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http://pubman.mpdl.mpg.de/cone/persons/resource/persons58745

Lehr,  Konrad
Research Department Fürstner, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

http://pubman.mpdl.mpg.de/cone/persons/resource/persons58380

Fürstner,  Alois
Research Department Fürstner, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Citation

Lehr, K., & Fürstner, A. (2012). An efficient route to the musk odorant (R,Z)-5-muscenone via base-metal-catalysis. Tetrahedron, 68(37), 7695-7700. doi:10.1016/j.tet.2012.05.085.


Cite as: http://hdl.handle.net/11858/00-001M-0000-000F-F0DC-3
Abstract
Muscenone® is a valuable perfume ingredient consisting of a mixture of the E- and Z-isomers of 1 in racemic form as the major constituents. Among them, it is the (R,Z)-isomer, which exhibits the most favorable musk character and by far the lowest threshold; for these superior olfactory properties, pure (R,Z)-1 has recently been commercialized too. We present an efficient route to this precious compound based on an iron-catalyzed cross coupling reaction, a molybdenum-catalyzed alkyne metathesis for the formation of the macrocyclic ring, and a nickel-catalyzed semi-hydrogenation.