Approaches to oximidines, lobatamides and related natural products: the coupling reactions of 3-iodoacrolein O-methyl oximes

✍ Scribed by Steven A Raw; Richard J.K Taylor

• Book ID: 104211407
• Publisher: Elsevier Science
• Year: 2000
• Tongue: French
• Weight: 94 KB
• Volume: 41
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)01862-1

✦ Synopsis

Both 2E-and 2Z-3-iodoacrolein O-methyl oximes are prepared in two steps from ethyl propiolate. Lithium-iodine exchange is effected and the resulting organolithium reagents added to several electrophiles, including styryl isocyanate which gives a conjugated O-methyl oxime enamide of the type found in the side chains of the oximidine, lobatamide and CJ-12950 natural products. The Pd(0) catalysed cross-coupling of these iodoalkenes is also explored.