ChemInform Abstract: Acetogenic Isoquinoline Alkaloids. Part 120. Directed Joint Total Synthesis of the Three Naphthylisoquinoline Alkaloids Dioncolactone A, Dioncopeltine A, and 5′-O-Demethyldioncophylline A.

✍ Scribed by Gerhard Bringmann; Wael Saeb; Martin Ruebenacker

• Publisher: John Wiley and Sons
• Year: 2010
• Weight: 38 KB
• Volume: 30
• Category: Article
• ISSN: 0931-7597
• DOI: 10.1002/chin.199923242

✦ Synopsis

Acetogenic Isoquinoline Alkaloids. Part 120. Directed Joint Total Synthesis of the Three Naphthylisoquinoline Alkaloids Dioncolactone A, Dioncopeltine A, and 5'-O-Demethyldioncophylline A.

-The first total synthesis of three title naphthylisoquinoline alkaloids dioncolactone A (VI), dioncopeltine A (VIII) and demethyldioncophylline A (XI) is presented involving the "lactone methodology" for the regio-and stereoselective construction of the biaryl axis. Thus, esterification of naphthylcarboxylic acid (I) with hydroxyquinoline (II), intramolecular coupling and atropo-diastereoselective lactone ring opening affords the naphthylisoquinoline skeleton (VII) in high optical purity. The corresponding atropoisomer (XII), obtained during reduction of compound (V) with achiral reductants as admixture, can be recyclized via the hydroxy aldehyde (XIII) which is reduced with comparable selectivity as the lactone (V) (dynamic kinetic resolution). -(BRINGMANN, GERHARD;