A New Route for the Synthesis of 1,4-Dicarbonyl Compounds: Synthesis of Jasmone,Dlhydrojasmone and a Prostaglandin Intermediate

1,4-Dicarbonyl compounds are versatile intermediates for the synthesis of a variety of natural products such as jasmonoids, prostanoids, steroids and terpenoids having a cyclopentenone or furan ring system. Although many synthetic routes for the preparation of these compounds are known and continue to appear¹, most of the existing methods involve lengthy procedures and are limited to the synthesis of 1,4-diketones. Herein, we report a convenient three step approach for the synthesis of 1,4-dicarbonyl compounds starting from tosyl methyl isocyanide² (TosMIC). This method is general for the preparation of 1,4-ketoaldehydes as well as 1,4-diketones.