A new ready route to 1,4-ketoaldehydes and 1,4-diketones with application to the synthesis of z-jasmone and dihydrojasmone

Iron-Catalyzed Reactions in Organic Synthesis

“…Thioesters 196 react with Grignard reagents in an analogous manner leading to the formation of corresponding ketone in good yield (eq 59) . This protocolfound application in the total synthesis of ( Z )-jasmone and dihydrojasmone 167d …”

Iron Catalysis in Synthetic Chemistry

“…Various functionalized acid chlorides, cyanides, and thioesters with primary, secondary, and tertiary alkyl and aryl Grignard reagentsdiorganozinc derivatives afforded the corresponding products in good-to-excellent yields under mild reaction condition (Table XXII) (153b, 179). Total synthesis of (Z)-jasmone and dihydrojasmone were done using this reaction (180). Fürstner et al (181) synthesized the key building blocks for a concise total synthesis of the actin-binding macrolides of the latrunculin family, like latrunculin B (Scheme 121a) and the musk odorant (R,Z)-5-muscenone.…”