131011-23-9Relevant academic research and scientific papers
Synthesis of Bridged Homoiridoids from Secologanin by Tandem-Knoevenagel-Hetero-Diels-Alder Reactions
Tietze, Lutz F.,Baertels, Christoph
, p. 155 - 160 (2007/10/02)
The tandem-Knoevenagel-hetero-Diels-Alder reaction of the chiral enantiomerically pure monoterpene glucoside secologanin (1) with 1,3-dicarbonyl compounds 6a-d and the analogous compounds 11a-b in the presence of ethylenediammonium diacetate as catalyst leads to the bridged cycloadducts 8a-d and 13a-b in 60-70percent yield, except for 8d.Compound 8b can be transformed into 9 by treatment with methanol and into 10 by treatment with water.The cycloadditions are highly regio- and stereoselective, affording only the bridged but not the annulated compounds as single diastereomers.
