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The palladium-catalyzed construction of the carbazole framework provides an efficient access to 3-hydroxy-6-methylcarbazole (glycozolinine) (5). Regioselective annulation of a pyran ring at glycozolinine (5) using either a C 5 - or a C 10 -building block leads to the pyrano[2,3-c]carbazole alkaloids glycomaurin (5,6-pyranoglycozoline, eustifoline-A) (2) and eustifoline-B (4), respectively...
The DIBAL‐H promoted reductive pyran ring opening of dialkylpyrano[3,2‐a]carbazoles provides a direct access to a broad range of prenyl‐ and geranyl‐substituted carbazoles. Formation of a pyran ring followed by reductive ring opening represents a new method for the introduction of prenyl and geranyl groups. In the course of the present work, we achieved the first total syntheses of the following eight...
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