A Versatile Solid Phase Synthesis of Lavendustin A and Certain Biologically Active Analogs

Reaction of aminomethylated polystyrene resin ( 8 ) with succinic anhydride, followed by esterification of the free carboxylic acid of the product 9 with 2,5-dihydroxybenzaldehyde ( 4 ), afforded the resin-linked aldehyde intermediate 10 . The key intermediate 10 was converted into the protein-tyrosine kinase inhibitor lavendustin A and certain analogs through reductive amination and reductive alkylation steps, followed by cleavage from the resin. This method enables the preparation of a wide variety of lavendustin A analogs using combinatorial chemistry and parallel synthesis techniques.