Total Synthesis of (+)-Tanikolide by a Traceless Stereoinduction Method Using Rhodium(II)-Catalyzed Oxonium Ylide Formation–[2,3]-Sigmatropic Rearrangement and NHC-Catalyzed Ring-Expansion Lactonization
| Autor: | Takayuki Yakura, Tomoya Fujiwara, Hisanori Nambu, Hikari Jinnouchi |
|---|---|
| Rok vydání: | 2016 |
| Předmět: |
chemistry.chemical_classification
010405 organic chemistry Stereochemistry 2 3-sigmatropic rearrangement Organic Chemistry chemistry.chemical_element Total synthesis 010402 general chemistry Ring (chemistry) 01 natural sciences 0104 chemical sciences Rhodium Catalysis chemistry Ylide Oxonium ion Divergent synthesis |
| Zdroj: | Synlett. 27:1106-1009 |
| ISSN: | 1437-2096 0936-5214 |
| DOI: | 10.1055/s-0035-1561341 |
| Popis: | The total synthesis of (+)-tanikolide was accomplished by a traceless stereoinduction method using the key steps of a Rh(II)-catalyzed oxonium ylide formation–[2,3]-sigmatropic rearrangement and an N-heterocyclic carbene-catalyzed ring-expansion lactonization of tetrahydrofurfural. This synthetic route is applicable to the divergent synthesis of tanikolide analogues. |
| Databáze: | OpenAIRE |
| Externí odkaz: |
|