(Z)-7-Nitro-3-Heptene as Central Intermediate for the Synthesis of Jasmone, Methyl Jasmonate, and γ Jasmolactone

Abstract

(Z)-7-Nitro-3-heptene is used as central intermediate in the synthesis of jasmone (13), methyl jasmonate (15), and γ-jasmolactone (16), three jasmin constituents.

Conjugate addition of the title nitro compound, by heterogeneous catalysis, to methyl vinyl ketone, or acrolein, or methyl acrylate, followed by Nef reaction, affords (Z)-undec-8-ene-2,5-dione, (Z)-1,4-dioxodec-7-ene, and (Z)-4-oxo-dec-7-enoic acid methyl ester respectively, which are easily converted into jasmone, methyl jasmonate and γ -jasmolactone.