Synthesis of γ-Oxoaldehydes and Their Related Compounds from Acrylaldehyde Diethyl Acetal

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  • アクリルアルデヒド-ジエチルアセタールを原料とするγ-オキソアルデヒド及び関連化合物の合成
  • アクリルアルデヒド ジエチルアセタール オ ゲンリョウ ト スル ガンマ オキ

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Abstract

This paper describes the synthesis of pheromones and jasmonoids from acrylaldehyde diethyl acetal (1). The synthetic route is shown in Scheme-1. <BR>The radical addition reaction of aldehyde with (1) was carried out with benzoyl peroxide as the initiator in N2 atomosphere. γ-Oxoaldehyde acetal [(6), (7), (8), (9)] was obtained as the major product by this reaction. <BR>cis-12-Nonadecen-9-one (14) was synthesized from 1, 1-diethoxy-4-oxododecanal (11) prepared from (7), by Wittig reaction in 62% yield. Similarly, cis-13-icosen-1O-one (15) and cis-5-undecen-2-one (16) were prepared from γ-oxoaldehyde in 6062% yield. <BR>Methyl jasmonate (18) and cis-jasmone (19) were synthesized from 2- (cis-2-pentenyl) -2-cyclopentenone (17) prepared from 4-oxo-cis-7-decenal (10), according to the published method. γ-Jasmolactone (21) was prepared from 1, 1-diethoxy-cis-7-decen-4-ol (20) by Jones oxidation in 88% yield.

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