Total syntheses of both enantiomers of amphirionin 4: A chemoenzymatic based strategy for functionalized tetrahydrofurans
| Autor: | Prasanth R. Nyalapatla, Arun K. Ghosh |
|---|---|
| Rok vydání: | 2017 |
| Předmět: |
Resolution (mass spectrometry)
010405 organic chemistry Stereochemistry Chemistry Organic Chemistry Enantioselective synthesis 010402 general chemistry Polyene 01 natural sciences Biochemistry Article Coupling reaction 0104 chemical sciences Stille reaction chemistry.chemical_compound Drug Discovery Side chain Proton NMR Enantiomer |
| Zdroj: | Tetrahedron. 73:1820-1830 |
| ISSN: | 0040-4020 |
| Popis: | The total syntheses of (−)-amphirionin-4 and (+)-amphirionin-4 have been achieved in a convergent and enantioselective manner. The tetrahydrofuranol cores of amphirionin-4 were constructed in optically active form by enzymatic resolution of racemic cis-3-hydroxy-5-methyldihydrofuran-2(3H)-one. The polyene side chain was efficiently synthesized using Stille coupling. The remote C8-stereocenter was constructed using the Nozaki-Hiyama-Kishi coupling reaction. Detailed 1H NMR studies of Mosher esters of (−)-amphirionin-4 and (+)-amphirionin-4 were carried out to support the assignment of the absolute configurations of the C-4 and C-8 asymmetric centers of amphirionin-4. |
| Databáze: | OpenAIRE |
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