64298-90-4Relevant articles and documents
Parallel and four-step synthesis of natural-product-inspired scaffolds through modular assembly and divergent cyclization
Oguri, Hiroki,Mizoguchi, Haruki,Oikawa, Hideaki,Ishiyama, Aki,Iwatsuki, Masato,Otoguro, Kazuhiko,Oemura, Satoshi
, p. 930 - 940 (2012/08/29)
By emulating the universal biosynthetic strategy, which employs modular assembly and divergent cyclizations, we have developed a four-step synthetic process to yield a collection of natural-product-inspired scaffolds. Modular assembly of building blocks onto a piperidine-based manifold 6, having a carboxylic acid group, was achieved through Ugi condensation, N-acetoacetylation and diazotransfer, leading to cyclization precursors. The rhodium-catalyzed tandem cyclization and divergent cycloaddition gave rise to tetracyclic and hexacyclic scaffolds by the appropriate choice of dipolarophiles installed at modules 3 and 4. A different piperidine-based manifold 15 bearing an amino group was successfully applied to demonstrate the flexibility and scope of the unified four-step process for the generation of structural diversity in the fused scaffolds. Evaluation of in vitro antitrypanosomal activities of the collections and preliminary structure - activity relationship (SAR) studies were also undertaken.
Syntheses of the racemates and the enantiomers of analogs of thalidomide alkylated in 3-position and determination of their absolute configuration
Knabe,Omlor
, p. 499 - 505 (2007/10/02)
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