Mohanrao, Raja ; Asokan, Aromal ; Sureshan, Kana M. (2014) Bio-inspired synthesis of rare and unnatural carbohydrates and cyclitols through strain driven epimerization Chemical Communications, 50 (51). pp. 6707-6710. ISSN 1359-7345
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Official URL: http://doi.org/10.1039/C4CC00868E
Related URL: http://dx.doi.org/10.1039/C4CC00868E
Abstract
We report a bio-inspired, strain driven epimerization of trans-ketals to cis-ketals through an enolate intermediate. Swern oxidation of a hydroxyl group adjacent to a trans-ketal effects both oxidation and its epimerization to cis-ketal. This novel and general strategy allows inversion of up to three contiguous stereocenters and has been illustrated by the synthesis of several unnatural/rare isomers of carbohydrates/cyclitols from their naturally abundant isomers.
| Item Type: | Article |
|---|---|
| Source: | Copyright of this article belongs to Royal Society of Chemistry. |
| ID Code: | 119888 |
| Deposited On: | 18 Jun 2021 06:19 |
| Last Modified: | 18 Jun 2021 06:19 |
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