ChemInform Abstract: Simple Designs for the Construction of Complex Trans-Fused Polyether Toxin Frameworks. A Linear Strategy Based on Entropically Favored Oxirane Ring Enlargement in Epoxycycloalkenes Followed by Carbon- Carbon or Carbon-Oxygen Bond-Form
| Autor: | José L. Ravelo, Jose A. Vera, Julio D. Martín, Dácil Zurita, Eleuterio Álvarez, Alicia Regueiro, Ricardo Perez, Maria Teresa Diaz |
|---|---|
| Rok vydání: | 2010 |
| Předmět: |
chemistry.chemical_classification
Stereochemistry Reinforced carbon–carbon Enantioselective synthesis chemistry.chemical_element General Medicine Ring (chemistry) Aldehyde Combinatorial chemistry chemistry.chemical_compound chemistry Fragmentation (mass spectrometry) Intramolecular force Tin Carbon–oxygen bond |
| Zdroj: | ChemInform. 25 |
| ISSN: | 0931-7597 |
| DOI: | 10.1002/chin.199449074 |
| Popis: | A successful design for the construction of trans-fused medium-size cy- clic ethers is described. The key features of the synthesis are as fol- lows: (i) intramolecular oxirane ring expansion in cycloalkenes to give bridged oxabicyclic systems and (ii) linear, one- or two-directional synthetic operations which generate external oxocycles in single reac- tion steps. The general approach involves the intramolecular addition of a stable γ-alkoxy-substituted allylstannane to an aldehyde carbonyl group, and the entire reaction is conducted in a one-pot process which includes the following: (i) vic-diol fragmentation from the bridged oxabicyclic precursor and (ii) Lewis acid-induced cyclization of the resulting aldehyde-allylic tin system. While the present strategy was mostly developed around racemic models, the potential for adoption of enantioselective features is immediate. The versatility, scope, limi- tations, and potential applications of the present technology are discussed in detail |
| Databáze: | OpenAIRE |
| Externí odkaz: |
|
Plný text