Suneel Kumar, Chepuri V. ; Ramana, Chepuri V. (2014) Tuning the regioselectivity of gold-catalyzed internal nitroalkyne redox: A cycloisomerization and [3 + 2]-cycloaddition cascade for the construction of spiro-pseudoindoxyl skeleton Organic Letters, 16 (18). pp. 4766-4769. ISSN 1523-7060
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Official URL: http://pubs.acs.org/doi/full/10.1021/ol502213w
Related URL: http://dx.doi.org/10.1021/ol502213w
Abstract
A simple domino process for the construction of the tricyclic core present in the spiro-pseudoindoxyl natural products has been developed. This involves two intramolecular events: the Au-catalyzed nitroalkyne redox leading to isatogen and its subsequent [3 + 2]-cycloaddition with a suitably positioned olefin. The option to modulate the size of the spiro-annulated ring, which is an important variable in this class of natural products, has been explored. Overall, this process molds a linear precursor into a tricyclic system with complete step, atom, and redox economy.
| Item Type: | Article |
|---|---|
| Source: | Copyright of this article belongs to American Chemical Society. |
| ID Code: | 105930 |
| Deposited On: | 01 Feb 2018 16:52 |
| Last Modified: | 01 Feb 2018 16:52 |
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