Copper and silicon mediated, HMPA-free, n+3 ring expansions for the construction of medium sized lactones and lactams: short synthesis of (+)-cis-lauthisan
| Autor: | William A. Maio, Mark A. Hatcher, Gary H. Posner |
|---|---|
| Rok vydání: | 2016 |
| Předmět: |
chemistry.chemical_classification
Ketone Silicon 010405 organic chemistry Chemistry Stereochemistry Organic Chemistry chemistry.chemical_element Epoxide Total synthesis 010402 general chemistry 01 natural sciences Biochemistry Copper 0104 chemical sciences chemistry.chemical_compound Drug Discovery Stereoselectivity |
| Zdroj: | Tetrahedron. 72:6025-6030 |
| ISSN: | 0040-4020 |
| DOI: | 10.1016/j.tet.2016.05.063 |
| Popis: | In this report, several new epoxide examples were united with β-silyl ketone enolates for the construction, after oxidative fragmentation, of ring expanded lactones, n+3 atoms in size. Importantly, azido lactones were found to be valuable in an extension of this protocol involving the n+3+p expansion into a series of hydroxyolefinic lactams. We also document a short, stereoselective total synthesis of (+)-cis-lauthisan and a new, cuprate-mediated and HMPA-free procedure for the generation of β-silyl silylenol ethers, useful in the environmentally-friendly construction of medium sized lactones. |
| Databáze: | OpenAIRE |
| Externí odkaz: |
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