A diastereoselective synthesis of boceprevir's gem-dimethyl bicyclic [3.1.0] proline intermediate from an insecticide ingredient cis-cypermethric acid
| Autor: | Vikas Gajare, Michael C. Lloyd, Martin E. Fox, Rashid Abdul Rehman Khan, Moses Babu Janagili, Veerabhadra Pratap Tadikonda, Bhaskar Kandagatla, Manpreet Singh, Rajesh Kumar Rapolu, Javed Iqbal, Malavika Banda, Sandip R. Khobare, Srinivasa Reddy Kallam, Rajender Datrika, Vilas Hareshwar Dahanukar, Siddaiah Vidavalur, Saikat Sen, Vishnuvardhan Reddy Eda, Srinivas Oruganti |
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| Rok vydání: | 2017 |
| Předmět: |
chemistry.chemical_classification
Bicyclic molecule 010405 organic chemistry Chemistry Stereochemistry Carboxylic acid Organic Chemistry 010402 general chemistry Ring (chemistry) 01 natural sciences Biochemistry 0104 chemical sciences Cyclopropane chemistry.chemical_compound Ingredient Boceprevir Drug Discovery Moiety Proline |
| Zdroj: | Tetrahedron. 73:4285-4294 |
| ISSN: | 0040-4020 |
| Popis: | An efficient multi-gram synthesis of (1R,2S,5S)-methyl 6,6-dimethyl-3-azabicyclo[3.1.0]hexane-2-carboxylate, a key chiral bicyclic proline fragment employed in the construction of the potent anti-HCV drug boceprevir, has been presented. The synthetic route commences with the readily available cis-cypermethric acid, a cheap source of the cyclopropane ring required in the targeted compound, and utilizes the cis-orientation of the 2,2-dichlorovinyl and carboxylic acid side arms, already present in the starting material, to effect a diastereoselective construction of the proline moiety. |
| Databáze: | OpenAIRE |
| Externí odkaz: |
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