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Preparation and Photochemistry of 3-O-Methylestra-1,3,5(10)-Triene-17beta-yl Cinnamates and 3-O-Methylestra-1,3,5(10)-Trien-17-one O-Cinnamoyl-17-Oximes
1 , 1 , * 2
1  Department of Chemistry, UAE University
2  Department of Chemistry, United Arab Emirates University

Abstract: 3-O-Methylestra-1,3,5(10)-triene-17beta-yl (E)-cinnamates and 3-O-methylestra-1,3,5(10)-trien-17-one O-(E)-cinnamoyl-17-oximes were prepared from the reaction of cinnamic acids with 3-O-methylestra-1,3,5(10)-trien-17-beta-ol and 3-O-methylestra-1,3,5(10)-trien-17-one 17-oxime, respectively, in the presence of PPh3-CBrCl3 in an Appel-type reaction. Under photolysis, the steroidal cinnamates underwent E-/Z-isomerisation, while the steroidal O-cinnamoyloximes underwent E-/Z-isomerisation concomitant with cleavage reactions.
Keywords: Steroids; estradiol; cinnamates; O-cinnamoyl oximes; Appel reaction; photochemistry; E-/Z-isomerisation