Jasmone, synthesis

Jacobson-Hugershofi synthesis benzothiazoles, 5, 135 Japp-KJingemann reaction JV-arylhydrazones from, 4, 337 1,2,4-triazole synthesis by, 5, 768 Jasmine lactone synthesis, 3, 847 Jasminine occurrence, 2, 626 y-Jasmolactone synthesis, 4, 674 cis-Jasmone synthesis, 1, 422, 427 Jatropham synthesis, 1, 426 Josephson junctions, 1, 359 Juliprospine... 

An alternative furan-based jasmone synthesis has been accomplished through oxidative cleavage of this heterocyclic ring (73AJC2671). Thus, the furan (85) was oxidized with Collins reagent to the enedione (86) and the conjugated double bond reduced with sodium dithionite. Base cyclization then gave pure (Z)-jasmone (Scheme 21). 

Although it has been known since 1938 that alkoxy-substituted alkyl cyclopropanecar-boxylates can be opened to 1,4-dicarbonyl compounds it was not until 1970 that the synthetic merit of this route to a valuable class of intermediates was recognized. In this year Wenkert and coworkers described the preparation of cyclopentenones from this type of cyclopropane via 1,4-diketones as outlined in equation 83 " . Shortly later McMurry and Glass have published a ds-jasmone synthesis following the same principle ... 

An attractive jasmone synthesis comes from Grieco. [89] A bicyclic ketone is obtained from the [2 -i- 2]-cycloaddition of dichloroketene to cyclopentadiene, followed by reduction with zinc. After Baeyer-Villiger oxidation, reduction to... 

---