An expeditious protocol for sesquiterpene-cored functionalized arenes from S-(-)-citronellal

Abstract

An expeditious straightforward synthesis of sesquiterpene-cored arenes functionalized with electron-withdrawing or donating substituents is described and illustrated by Michael addition of S-(-)-citronellal on functionalized 2H-pyran-2-one in a single step at room temperature. The reaction was further generalized by synthesizing isoprenylated 9,10-dihydrophenanthrene-2-carbonitrile using 5,6-dihydro-2-oxo-4-sec-amino-2H-benzo[h]chromene-3-carbonitriles and S-(-)-citronellal under similar reaction conditions.