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Parallel and four-step synthesis of natural-product-inspired scaffolds through modular assembly and divergent cyclization.


ABSTRACT: 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.

SUBMITTER: Oguri H 

PROVIDER: S-EPMC3388883 | biostudies-other | 2012

REPOSITORIES: biostudies-other

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Parallel and four-step synthesis of natural-product-inspired scaffolds through modular assembly and divergent cyclization.

Oguri Hiroki H   Mizoguchi Haruki H   Oikawa Hideaki H   Ishiyama Aki A   Iwatsuki Masato M   Otoguro Kazuhiko K   Omura Satoshi S  

Beilstein journal of organic chemistry 20120622


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 cycloadditi  ...[more]

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