Studies of a Diazo Cyclopropanation Strategy for the Total Synthesis of (−)-Lundurine A
| Autor: | Jin Gong, Hao Song, Shuai-Jiang Jin, Hongxiu Huang, Yong Qin, Dan Zhang |
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| Rok vydání: | 2015 |
| Předmět: |
chemistry.chemical_classification
Biological Products biology Cyclopropanation Stereochemistry Organic Chemistry Side reaction Total synthesis Hydrazone Stereoisomerism General Chemistry biology.organism_classification Catalysis chemistry.chemical_compound Alkaloids chemistry Bamford–Stevens reaction Polycyclic Compounds Diazo Kopsia Azo Compounds Carbene |
| Zdroj: | Chemistry - A European Journal. 21:13284-13290 |
| ISSN: | 0947-6539 |
| DOI: | 10.1002/chem.201502011 |
| Popis: | The bioactive Kopsia alkaloids lundurines A-D are the only natural products known to contain indolylcyclopropane. Achieving their syntheses can provide important insights into their biogenesis, as well as novel synthetic routes for complex natural products. Asymmetric total synthesis of (-)-lundurine A has previously been achieved through a Simmons-Smith cyclopropanation strategy. Here, the total synthesis of (-)-lundurine A was carried out using a metal-catalyzed diazo cyclopropanation strategy. In order to avoid a carbene CH insertion side reaction during cyclopropanation of α-diazo- carboxylates or cyanides, a one-pot, copper-catalyzed Bamford-Stevens diazotization/diazo decomposition/cyclopropanation cascade was developed, involving hydrazone. This approach simultaneously generates the C/D/E ring system and the two chiral quaternary centers at C2 and C7. |
| Databáze: | OpenAIRE |
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