Studies directed toward the synthesis of cryptoheptine.
Synthesis of 5,10-dihydro-10-methylindolo[3, 2-b][1]benzazepin-12(11H)-one (2), an isomer of the reported structure for cryptoheptine (1), is presented. Attempts to convert 2 to 1 led to 10-methylindolo[3,2-b][1]benzazepin-12-one (10), an oxidation product of 2 and presumably 1. These results highlight the potential instability of cryptoheptine and cast doubt on its proposed structure.
Zhang
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Shaman Pharmaceuticals, 213 East Grand Avenue, South San Francisco, California 94080-4812, USA.
Bierer
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D000354:Africa, Western; D001552:Benzazepines / Q000737:chemistry*; D002855:Chromatography, Thin Layer; D007004:Hypoglycemic Agents / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D010946:Plants, Medicinal / Q000737:chemistry*
D001552:Benzazepines; D007004:Hypoglycemic Agents; C410926:cryptoheptine