Abstract
Cyclohexanetetrols belong to the family of cyclitols, a class of natural products known for their diverse bioactivity. Their synthesis has been reported using hydrogen peroxide as a green oxidant and water or tert-butanol as a solvent. Due to the high polarity of those compounds, a green approach for their isolation from aqueous solutions can be challenging. Here, we report the stereoselective synthesis of (±)-trans,trans-cyclohexane-1,2,4,5-tetraol combined with a novel isolation method, where is possible the isolation of the product in excellent yield without the need for derivatization, column chromatography or organic solvent extraction.
| Original language | English |
|---|---|
| Pages (from-to) | 142-148 |
| Number of pages | 7 |
| Journal | AppliedChem |
| Volume | 2 |
| Issue number | 3 |
| DOIs | |
| Publication status | Published - Sept 2022 |
Bibliographical note
Publisher Copyright:© 2022 by the authors.
Funding
This research was funded by Fundação para a Ciência e Tecnologia (FCT) (Ref. PTDC/QUI-QOR/32008/2017, PTDC/CTM-CTM/29869/2017, UIDB/04138/2020, UIDP/04138/2020, UIDB/04567/2020 and UIDP/04567/2020). This project has received funding from the European Union’s Horizon 2020 research and innovation program under grant agreement No 951996. The NMR spectrometer is part of the National NMR Network (PTNMR) and are partially supported by Infrastructure Project No 022161 (co-financed by FEDER through COMPETE 2020, POCI and PORL and FCT through PIDDAC).
| Funders | Funder number |
|---|---|
| European Regional Development Fund | |
| Programa Operacional Temático Factores de Competitividade | |
| Fundação para a Ciência e a Tecnologia | UIDP/04567/2020, UIDB/04567/2020, UIDB/04138/2020, PTDC/QUI-QOR/32008/2017, UIDP/04138/2020, PTDC/CTM-CTM/29869/2017 |
| Horizon 2020 Framework Programme | 951996, 022161 |
Keywords
- cyclohexane-1,2,4,5-tetraol
- green chemistry
- organocatalysis
- trans-bis-dihydroxylation