Synthesis of (+)-Methyl (R,E)-6-Benzyloxy-4-hydroxy-2-hexenoate and Its Mesylate Derivative

Synthesis of (+)-Methyl (R,E)-6-Benzyloxy-4-hydroxy-2-hexenoate and Its Mesylate Derivative

Methyl (E)-6-benzyloxy-4-hydroxy-2-hexenoate is prepared in both racemic and enantiopure form through reaction between (2-benzyloxy)ethyloxirane and the dianion of phenylselenoacetic acid followed by esterification with diazomethane, oxidation to the selenoxide and subsequent pyrolysis in 72% overal...

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Veröffentlicht in:Synthetic communications 1995-02, Vol.25 (3), p.331-342
Hauptverfasser: March, P. de, Figueredo, M., Font, J., Monsalvatje, M.
Format: Artikel
Sprache:eng
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Zusammenfassung:Methyl (E)-6-benzyloxy-4-hydroxy-2-hexenoate is prepared in both racemic and enantiopure form through reaction between (2-benzyloxy)ethyloxirane and the dianion of phenylselenoacetic acid followed by esterification with diazomethane, oxidation to the selenoxide and subsequent pyrolysis in 72% overall yield.
ISSN:0039-7911
1532-2432
DOI:10.1080/00397919508011364