A new route for the synthesis of 1,4-dicarbonyl compounds: synthesis of jasmone, dlhydrojasmone and a prostaglandin intermediate

Abstract

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 appear, 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 isocyanide(TosMIC). This method is general for the preparation of 1,4-ketoaldehydes as well as 1,4-diketones.