A Photochemical Approach to the Fully Functionalized Ring System of Chilinene, a Key Alkaloid of the Berberine Family

✍ Scribed by Paul H. Mazzocchi; Cliff R. King; Herman L. Ammon

• Book ID: 104227187
• Publisher: Elsevier Science
• Year: 1987
• Tongue: French
• Weight: 200 KB
• Volume: 28
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)95444-3

✦ Synopsis

The fully functionalized ring system of the berberine alkaloid chilinene has been prepared in a seven step synthesis. Key steps in the synthesis are the photocyclization of an imide-thioether and the oxidative formation with Pb(OAc), of a novel hexacyclic orthoester which led directly to the desired product.

Chilinene (1) , a member of the berberine alkaloid family ,has so far yielded to only one synthetic approach.1 A number of investigations2*3 on the synthesis of the functionalized ring system of 1 and other members of the berberine family have focused on 2 as a key intermediate. Without exception attempts to convert 2 to a functionalized natural product analog have resulted in undesireable cleavage reactions and failure.4