Total Synthesis of Liangshanone
| Autor: | Xiao-Yu Liu, Fen Mi, Hongxiu Huang, Yong Qin, Huan He, Chunxin Li, Feng-Peng Wang |
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| Rok vydání: | 2020 |
| Předmět: |
chemistry.chemical_classification
Annulation Natural product 010405 organic chemistry Alkene Stereochemistry Enantioselective synthesis Total synthesis General Medicine General Chemistry 010402 general chemistry 01 natural sciences Catalysis Cycloaddition 0104 chemical sciences chemistry.chemical_compound chemistry Aldol reaction Intramolecular force |
| Zdroj: | Angewandte Chemie (International ed. in English). 59(52) |
| ISSN: | 1521-3773 |
| Popis: | The first total synthesis of liangshanone, a hexacyclic ent-kaurane diterpenoid alkaloid, has been completed. Its intricate cagelike framework was assembled through several key transformations, including an oxidative dearomatization/Diels-Alder (OD/DA) cycloaddition sequence, a tandem alkene cleavage/Mannich cyclization, a Robinson-type annulation, and an intramolecular aldol reaction. Notably, an organocatalytic enantioselective α-hydroxymethylation process allowed the preparation of an enantiomerically enriched tricyclic intermediate that should enable asymmetric access to the target natural product. |
| Databáze: | OpenAIRE |
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