A fast and straightforward route towards the synthesis of the lissoclimide class of anti-tumour agents
| Autor: | K. Yoganathan, Nguyen Quang Vu, Tuan Minh Nguyen, Mark S. Butler, Jean-Jacques Youte, Ying San Ho, Jacelyn Lau, Christina L. L. Chai, Benjamin S.W. Tan, Angie Cheong |
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| Rok vydání: | 2010 |
| Předmět: |
inorganic chemicals
chemistry.chemical_classification Double bond Stereochemistry organic chemicals Organic Chemistry technology industry and agriculture Enantioselective synthesis Biochemistry Chemical synthesis chemistry.chemical_compound Aldol reaction Succinimide chemistry Drug Discovery polycyclic compounds Moiety Aldol condensation Protecting group |
| Zdroj: | Tetrahedron. 66:9270-9276 |
| ISSN: | 0040-4020 |
| DOI: | 10.1016/j.tet.2010.09.031 |
| Popis: | The synthesis of the chiral core structure of the lissoclimide class of anti-tumour agents containing three rings, including a chiral succinimide subunit and an exocyclic double bond, has been investigated. The compound 7 was obtained, without the use of any protecting groups for the alcohol at C-12, via an asymmetric boron-mediated aldol addition as the key step to install the chiral centres of the rare succinimido methanol moiety. This was followed by a sequence of lactonisation, microwave-assisted amidation and imidation reactions. |
| Databáze: | OpenAIRE |
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