Total Synthesis of (+)-Asteltoxin
| Autor: | Jin Kun Cha, Heejin Kim, J. Venkat Raman, Khee Dong Eom |
|---|---|
| Rok vydání: | 2003 |
| Předmět: |
chemistry.chemical_classification
Steric effects Bicyclic molecule Chemistry Stereochemistry Convergent synthesis Total synthesis Stereoisomerism General Medicine General Chemistry Mycotoxins Biochemistry Aldehyde Phosphonate Catalysis Silyl ether chemistry.chemical_compound Aspergillus Colloid and Surface Chemistry Pyrones Stereoselectivity Tetrahydrofuran |
| Zdroj: | Journal of the American Chemical Society. 125:5415-5421 |
| ISSN: | 1520-5126 0002-7863 |
| DOI: | 10.1021/ja034332q |
| Popis: | A convergent synthesis of (+)-asteltoxin (1) has been achieved by the Horner-Emmons olefination of bis(tetrahydrofuran) aldehyde 53 and alpha-pyrone phosphonate 5. A key step features the stereoselective construction of a sterically congested quaternary center embedded in the densely functionalized bis(tetrahydrofuran) subunit by a Lewis acid-catalyzed, pinacol-type rearrangement of an epoxy silyl ether. This pivotal rearrangement methodology parallels the proposed biosynthetic pathway of 1 and is ripe for applications to the stereocontrolled synthesis of structurally complex natural products. |
| Databáze: | OpenAIRE |
| Externí odkaz: |
|