Abstract
The pyrido[4,3-b]carbazole alkaloid, ellipticine, was attracting considerable interest for many years due to its pronounced antitumor activity. We review the most important achievements in the field of ellipticine synthesis and its derivatives since 2012.
Highlights
Nagarajan et al.[32] reported a simple and efficient route to the synthesis of ellipticine quinone 12 (Scheme 3) from isatin 4
Synthesis of ellipticine quinone 12. Their synthesis commenced with the preparation of 9-benzyl-1,4-dimethylcarbazoles 15 and 16 from the corresponding 1,4-dimethylcarbazoles, which can be readily prepared by literature methods (Scheme 5)
The reaction of 31 with quinoline-3carboxaldehyde in the presence of TMG in MeOH followed by oxidation with Dess−Mar n periodinane (DMP) in DCM/ AcOH (9:1) at room temperature gave the ketone 49 in 80% yield
Summary
Nagarajan et al.[32] reported a simple and efficient route to the synthesis of ellipticine quinone 12 (Scheme 3) from isatin 4. Ellipticine quinone 12 was obtained in 3 steps and 67.6% overall yield (Scheme 8). Treatment of 31 with 2-methylnicotinaldehyde in the presence of 1,1,3,3-tetramethylguanidine (TMG) in MeOH at room temperature followed by oxidation using IBX afforded the ketone 45 in 84% yield.
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