A revised structure for the marine bromoindole derivative citorellamine

✍ Scribed by Robert M. Moriarty; Deborah M. Roll; Yi-Yin Ku; Chad Nelson; Chris M. Ireland

• Publisher: Elsevier Science
• Year: 1987
• Tongue: French
• Weight: 200 KB
• Volume: 28
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(01)80979-5

✦ Synopsis

The structure of citorellamine has been revised and confirmed by total synthesis to be 2 instead of _I_. Recently structure 1 was proposed for the marine natural product citorellamine.2 This assignment was based upon interpretation of spectral data, particularly rapidly exchangeable lH NMR (DMSO-d6) signals at 611.61 (br s, 1H) and 9.36 (br s, 2H) attributed to the indolic NH and primary amino groups, respectively. High resolution EIMS measurements indicated ClIH13BrN2S as the molecular formula and Raney nickel reduction yielded 3-methylindole.