ORGLIST:Synthesis of methyl farnesoate

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From: Paul D. Jones (pdjones$##$ucdavis.edu)
Date: Wed Sep 01 2004 - 14:37:48 EDT


Greetings,

I am trying to synthesize methyl farnesoate from farnesol. I have been
following the methods of Corey (JACS, 1968, pg. 5616) and Prestwich (Syn.
Commun. 1990, pg. 3125) to synthesis E,E-farnesal. Both references utilize
MnO2 as the oxidant. I am finding large amounts of a by-product which looks
to be the Z-E isomer. I have tried varying the reaction temp (0 C -> rt)
and reaction time (0.5 hr -> 16hr) with little improvement. Can anyone
suggest a good work around? Does anyone know of a good supplies for
E,E-methylfarnesoate?

Thanks

Paul

================================
Paul D. Jones, Ph.D.
NIH Postdoctoral Fellow
Department of Entomology &
Cancer Research Center
University of California, Davis
Davis, CA 95616
(530) 754-8884
================================

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