80054-41-7Relevant academic research and scientific papers
Resolution of an iridoid synthon, gastrolactol, by means of dynamic acetylation and lipase-catalyzed alcoholysis
Santangelo,Rotticci,Liblikas,Norin,Unelius
, p. 5384 - 5387 (2007/10/03)
A short synthetic route to asymmetric iridoids was developed. The three key steps were an intramolecular [4 + 2] cycloaddition reaction of an enamine derivative of 8-oxocitral (2), a dynamic acetylation, and an enzymatic resolution of the gastrolactyl acetates 5a and 5b, iridoids with three stereocenters. Some regio- and stereoselective heterogeneous catalytic hydrogenations of double bonds in iridoid aglucones were discussed.
Investigations of the Biosynthesis of Indole Alkaloids. Feeding Experiments with Synthetic Radioactively Labelled Monoterpene Aldehydes
Battersby, Alan R.,Thompson, Mervyn,Gluesenkamp, Karl-Heinz,Tietze, Lutz-F.
, p. 3430 - 3438 (2007/10/02)
Oxidation of citral (8a/8b) with selenium oxide using different reaction conditions gave the hydroxy aldehydes 4a/4b and the dialdehydes 5a/b.Reduction of 5a/b with potassium borohydride in the presence of LiCl led to the hydroxy aldehyes 4c/d.Feeding experiments with the corresponding tritiated compounds 4a - d and 5a/b to Catharanthus roseus G.Don indicate that 4a/b, 4c/d, and 5a/b are biogenetic precursors of secologanin (3) and the indole alkaloids of the Corynanthe, Aspidosperma, and Iboga type.
