A NOVEL SYNTHESIS OF ROYAL JELLY ACIDS AND QUEEN SUBSTANCE BY THE FIVE CARBON HOMOLOGATION USING β-VINYL-β-PROPIOLACTONE

descriptionPublicationkeyboard_double_arrow_right Article 01 Feb 1982 English Publisher:Oxford University Press (OUP)Journal:Chemistry Letters, volume 11, pages 219-220 (issn: 0366-7022, eissn: 1348-0715,

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Authors: Tamotsu Fujisawa; Toshio Sato; Toshiyuki Itoh;

doi: 10.1246/cl.1982.219

A NOVEL SYNTHESIS OF ROYAL JELLY ACIDS AND QUEEN SUBSTANCE BY THE FIVE CARBON HOMOLOGATION USING β-VINYL-β-PROPIOLACTONE

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Abstract

Abstract 10-Hydroxy-(E)-2-decenoic acid, (E)-2-decenedioic acid (Royal jelly acids), and 9-oxo-(E)-2-decenoic acid (queen substance) were synthesized via 10-hydroxy-3-decenoic acid and 9,9-ethylenedioxy-3-decenoic acid, respectively, prepared easily by the regioselective ring-opening reaction of β-vinyl-β-propiolactone with Grignard reagents in the presence of copper(I) catalyst.

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