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

1996/01/01 by Rajesh Devraj, Mark Cushman · 2 citations
Medicine · Biochemistry, Genetics and Molecular Biology · Chemistry · #Microbial Natural Products and Biosynthesis #Chemical Synthesis and Analysis #Synthetic Organic Chemistry Methods

paper · doi:10.1021/jo961719l

openalex publication_date 1996/01/01 · openalex created_date 2025/10/10 · openalex updated_date 2026/06/26

Abstract

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.

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