Total synthesis of (+)-UCS1025A based on a sequential Michael-retro Michael strategy featuring one-pot six-step cascade reaction
| Autor: | Tetsu Tsubogo, Ryo Kosuge, Hiromi Uchiro, Ryota Sano |
|---|---|
| Rok vydání: | 2018 |
| Předmět: |
chemistry.chemical_classification
010405 organic chemistry Chemistry Carboxylic acid education Organic Chemistry Total synthesis Primary alcohol 010402 general chemistry behavioral disciplines and activities 01 natural sciences Biochemistry Combinatorial chemistry humanities 0104 chemical sciences Cascade reaction Intramolecular force Drug Discovery Electrophile |
| Zdroj: | Tetrahedron Letters. 59:704-707 |
| ISSN: | 0040-4039 |
| DOI: | 10.1016/j.tetlet.2017.12.025 |
| Popis: | The asymmetric total synthesis of UCS1025A is accomplished by establishing a novel and efficient method for the construction of a tricyclic pyrrolizidinone skeleton based on a sequential Michael-retro Michael strategy. The key step is a one-pot six-step cascade reaction including oxidation of a primary alcohol to the corresponding carboxylic acid, a retro thio-Michael reaction, and an intramolecular oxy-Michael reaction. This newly-developed synthetic strategy inspired by “masked” electrophilic character of tricyclic pyrrolizidinone is efficient and high-yielding compared to that developed in previously-reported total syntheses. |
| Databáze: | OpenAIRE |
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