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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 Rübenacker

Publisher: Elsevier Science
Year: 1999
Tongue: French
Weight: 645 KB
Volume: 55
Category: Article
ISSN: 0040-4020
DOI: 10.1016/s0040-4020(98)01040-0

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✦ Synopsis

The first total synthesis of the three antimalarial naphthylisoquinoline alkaloids di0ncolactone A (4), dioncopeltine A (5), and 5'-O-demethyidioncophylline A ( 6) is described. The regio-and stereoselective construction of the biaryl axes was achieved through the 'lactone methodology', by ester-type prefixation of the two molecular moieties, intramolecular coupling, and atropo-diastereoselective cleavage of the iactone auxiliary bridge. As a novel alternative, the configuration at the axis may be installed by atroposelective hydroxy aldehyde reduction through dynamic kinetic resolution.

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