Sundaram, G. S. M. ; Venkatesh, C. ; Kumar, U. K. Syam ; Ila, H. ; Junjappa, H. (2004) A concise formal synthesis of alkaloid cryptotackiene and substituted 6H-indolo[2,3-b]quinolines Journal of Organic Chemistry, 69 (17). pp. 5760-5762. ISSN 0022-3263
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Official URL: http://pubs.acs.org/doi/abs/10.1021/jo049227t
Related URL: http://dx.doi.org/10.1021/jo049227t
Abstract
A five-step formal synthesis of alkaloid cryptotackiene and its 2-formyl, 11-methyl/phenyl derivatives involving conjugate addition of enolate anion from cyclohexanone (or 4-methylcyclohexanone) to bis[(methylsulfanyl)methylene]-2-oxindole followed by heterocyclization in the presence of ammonium acetate as the key step has been developed. The 11-methylsulfanyl group in the initial precursor can be either desulfurized (Raney Ni) or replaced by methyl/phenyl groups via nickel-catalyzed cross-coupling reaction with appropriate Grignard reagents.
| Item Type: | Article |
|---|---|
| Source: | Copyright of this article belongs to American Chemical Society. |
| ID Code: | 15277 |
| Deposited On: | 13 Nov 2010 13:01 |
| Last Modified: | 03 Jun 2011 04:46 |
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