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

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Title: Parallel and four-step synthesis of natural-product-inspired scaffolds through modular assembly and divergent cyclization
Authors: Oguri, Hiroki Browse this author →KAKEN DB
Mizoguchi, Haruki Browse this author
Oikawa, Hideaki Browse this author →KAKEN DB
Ishiyama, Aki Browse this author
Iwatsuki, Masato Browse this author
Otoguro, Kazuhiko Browse this author
Ōmura, Satoshi Browse this author
Keywords: chemical diversity
divergent cyclization
indole alkaloids
modular assembly
rhodium-catalyzed cyclization-cycloaddition
skeletal and stereochemical diversity
Issue Date: 22-Jun-2012
Publisher: Beilstein-Institut
Journal Title: Beilstein Journal of Organic Chemistry
Volume: 8
Start Page: 930
End Page: 940
Publisher DOI: 10.3762/bjoc.8.105
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.
Type: article
Appears in Collections:理学院・理学研究院 (Graduate School of Science / Faculty of Science) > 雑誌発表論文等 (Peer-reviewed Journal Articles, etc)

Submitter: 大栗 博毅

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