Synthesis of cinnamyl-sesamol derivatives
Received: 5 January 2009 / Accepted: 14 March 2009 / Published online: 3 December 2009
Ó Springer Science+Business Media BV 2009
Abstract A simple synthetic route to cinnamyl-sesamols has been developed
starting from sesamol via Claisen rearrangement followed by oleﬁn metathesis
Keywords Cinnamyl-sesamol Á Oleﬁn metathesis Á Insect control Á
Cinnamyl-sesamol derivatives, for example, 2-methoxy-4,5-methylenedioxy-cinna-
mylbenzene 1 and derivatives, have been found in the heartwood of Dalbergia
retusa [1, 2], are useful insect control , particularly as insect chemosteriants .
But, to our knowledge, the general synthetic route to these type of compounds has
not been reported. In this paper, we would like to report the synthesis of 1 and its
aromatic analogues by oleﬁn metathesis reaction (Fig. 1).
Our synthetic route to cinnamyl-sesamol derivatives is outlined in Scheme 1.
Cinnamyl-sesamol 1 would be obtained starting from sesamol via introduction of
cinnamyl group by Claisen rearrangement followed by methylation. Various
aromatic derivatives would be obtained from terminal oleﬁn 2 via Heck, Suzuki-
type coupling or oleﬁn metathesis reaction.
Along the literature procedure , sesamol was treated with sodium metal and
cinnamyl bromide in reﬂuxing toluene to produce phenolic compound 3 in 42%
yield (Scheme 2). After the methylation of hydroxyl group of 3, the desired product
1 was derived in 92% yield.
S. Tanimori (&) Á K. Watanabe Á M. Kirihata
Department of Bioscience and Informatics, Graduate School of Life and Environmental Sciences,
Osaka Prefecture University, 1-1 Gakuen-cho, Naka-ku, Sakai, Osaka 599-8531, Japan
Res Chem Intermed (2009) 35:909–917