Approach to cis-Phlegmarine Alkaloids via Stereodivergent Reduction: Total Synthesis of (+)-Serratezomine E and Putative Structure of (−)-Huperzine N
A unified strategy for the synthesis of the cisphlegmarine group of alkaloids is presented, leading to the first synthesis of serratezomine E (1) as well as the putative structure of huperzine N (2). A contrasteric hydrogenation method was developed based on the use of Wilkinson's catalyst, whi...
| Authors: | , , , , |
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| Format: | article |
| Status: | Versión aceptada para publicación |
| Publication Date: | 2015 |
| Country: | España |
| Institution: | Varias* (Consorci de Biblioteques Universitáries de Catalunya, Centre de Serveis Científics i Acadèmics de Catalunya) |
| Repository: | Recercat. Dipósit de la Recerca de Catalunya |
| OAI Identifier: | oai:recercat.cat:2445/128419 |
| Online Access: | https://hdl.handle.net/2445/128419 |
| Access Level: | Open access |
| Keyword: | Alcaloides Compostos heterocíclics Síntesi orgànica Productes naturals Alkaloids Heterocyclic compounds Organic synthesis Natural products |
| Summary: | A unified strategy for the synthesis of the cisphlegmarine group of alkaloids is presented, leading to the first synthesis of serratezomine E (1) as well as the putative structure of huperzine N (2). A contrasteric hydrogenation method was developed based on the use of Wilkinson's catalyst, which allowed the facial selectivity of standard hydrogenation to be completely overturned. Calculations were performed to determine the mechanism, and structures for huperzines M and N are reassigned. |
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