Coupling reactions of methoxybutenynyl copper - a facile route to substituted indoles

✍ Scribed by George A. Kraus; Kevin Frazier

• Publisher: Elsevier Science
• Year: 1978
• Tongue: French
• Weight: 352 KB
• Volume: 19
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(01)85592-1

✦ Synopsis

Cuprous acetylide coupling reactions with aromatic compounds afford an efficient and operationally convenient approach to the synthesis of aromatic natural products.' This method has been recently utilized for the synthesis of junipal.2 In connection with research directed toward the synthesis of indole alkaloids, we report the preparation and reactions of L, a versatile and H cu-c =C hitherto unreported copper acetylide. This compound can be prepared from commercially available methoxybutenyne3 by a modification4 of the method of Castro5 in 75% yield. This air-sensitive yellow solid reacts with aryl