Synthesis of 3-vinyl-2,5-dihydrofuran ring system via enyne metathesis.
An efficient route, starting from but-3-en-1,2-diol, is described to synthesize racemic diastereoisomeric (5-ethoxy-4-vinyl-2,5-dihydrofuran-2-yl) methanol derivatives. Acyclic enyne intermediates having the alkyne moiety directly connected to the asymmetric carbon atom of an acetal were obtained in two steps. These reactive substrates were then subjected to ruthenium-catalyzed enyne metathesis to produce the target compounds in racemic form. The relative configurations were determined by NOE proton NMR experiments. Similar strategy starting from (2S)-but-3-en-1,2-diol was proposed to provide pure enantiomers.
Vuong
Sophie
S
Université de Poitiers, UMR 6514 CNRS, Synthèse et Réactivité des Substances Naturelles, 40 Avenue du Recteur Pineau, F-86022 Poitiers cedex, France.
Rodriguez-Fernandez
M Mercedes
MM
Renoux
Brigitte
B
Len
Christophe
C
D000475:Alkenes / Q000737:chemistry*; D000480:Alkynes / Q000737:chemistry*; D002244:Carbon / Q000737:chemistry; D005663:Furans / Q000138:chemical synthesis* / Q000737:chemistry*; D013237:Stereoisomerism
D000475:Alkenes; D000480:Alkynes; D005663:Furans; D002244:Carbon; C039281:furan