Total synthesis of diazonamide A
| Autor: | Joseph Carpenter, Robert R. Knowles, Simon B. Blakey, Ian Mangion, Akio Kayano, Christopher J. Sinz, David W. C. MacMillan |
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| Rok vydání: | 2011 |
| Předmět: | |
| Zdroj: | Chem. Sci.. 2:308-311 |
| ISSN: | 2041-6539 2041-6520 |
| DOI: | 10.1039/c0sc00577k |
| Popis: | A total synthesis of the marine natural product diazonamide A (1) has been accomplished. This work features a highly stereoselective synthesis of the C(10) quaternary center and the central furanoindoline core enabled by an iminium-catalyzed alkylation–cyclization cascade. Additionally, a magnesium-mediated intramolecular macroaldolization and a palladium-catalyzed tandem borylation/annulation were developed to enable the closure of the two 12-membered macrocycles of diazonamide A. This synthesis involves 20 steps in its longest linear sequence and proceeds in 1.8% overall yield. |
| Databáze: | OpenAIRE |
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