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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. |
| Rights: | http://creativecommons.org/licenses/by/2.0/ |
| Type: | article |
| URI: | http://hdl.handle.net/2115/49572 |
| 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)
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Submitter: 大栗 博毅
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