Parallel synthesis of natural product-like polyhydroxylated pyrrolidine and piperidine alkaloids
Molecular Diversity(2010)
摘要
The preparation of natural product-like polyhydroxylated pyrrolidine and piperidine alkaloids using a combination of solid– and solution-phase organic synthesis is described. The key intermediates, enantiopure five- or six-membered tri- O -benzyl cyclic nitrones, were efficiently prepared on solid support from accessible chiral furanosides and pyranosides, respectively. The substituent diversity was achieved by a diastereoselective addition of a variety of Grignard reagents to the cyclic nitrones in solution-phase synthesis. All reaction steps and work-up procedures were modified to allow the use of automated equipment. A 36-membered demonstration library with three diversity elements (core, configuration, and substituent) was prepared in good yield and purity.
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关键词
Natural Product-like library,Solid-phase organic synthesis,Alkaloids,Substituent diversity,Core diversity,Stereogenic diversity,Privileged scaffolds
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