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A [2 + 2] Photocycloaddition-Fragmentation Approach toward the Carbon Skeleton of cis-Fused Lycorine-type Alkaloids
Maike H Wahl1, Christian Jandl1, Thorsten Bach1
1Department Chemie and Catalysis Research Center (CRC) , Technische Universität München , Lichtenbergstrasse 4 , 85747 Garching , Germany.
Abstract:
Starting from isoquinolones, the cis-selective annulation of six-membered rings was possible employing cyclobutenes as olefin components in a [2 + 2] photocycloaddition-fragmentation approach (nine examples, 54-80% yield). The developed sequence enables a conceptually new entry to cis-fused lycorine-type alkaloids of the Amaryllidaceae family with the complete carbon skeleton being successfully assembled. A subsequent von Braun-type reaction emphasized the biological relation between lycorine- and homolycorine-type alkaloids providing a synthetic tool to access this class of natural products.
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