Cyclization of Oxindolic methylketones with acid : A rapid synthesis of (±)-aspidofractinine

✍ Scribed by Dominique Cartier; Mohammed Ouahrani; Jean Lévy

• Book ID: 104229774
• Publisher: Elsevier Science
• Year: 1989
• Tongue: French
• Weight: 246 KB
• Volume: 30
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)99622-9

✦ Synopsis

The oxindolic methylketone Z. was cyclized in one step fo the hexacyclic ketolactam 9 with acid. (?)-Aspidofractinine a was prepared by sequential reduction of 3. The model oxindolic methylketone 11, when reacted with acid, gave compounds J-2 and w.

The intra-molecular cyclization of a methylketone onto the oxindolic lactam group (scheme 1) has been first

developed by Ban' : he converted Q to an iminoether (u, which proved suitable for a base-catalyzed (NaHIDMSO)