{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,10,12]],"date-time":"2025-10-12T02:57:53Z","timestamp":1760237873076,"version":"build-2065373602"},"reference-count":15,"publisher":"MDPI AG","issue":"3","license":[{"start":{"date-parts":[[2022,7,12]],"date-time":"2022-07-12T00:00:00Z","timestamp":1657584000000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"name":"Funda\u00e7\u00e3o para a Ci\u00eancia e Tecnologia (FCT)","award":["PTDC\/QUI-QOR\/32008\/2017","PTDC\/CTM-CTM\/29869\/2017","UIDB\/04138\/2020","UIDP\/04138\/2020","UIDB\/04567\/2020","UIDP\/04567\/2020","951996","022161"],"award-info":[{"award-number":["PTDC\/QUI-QOR\/32008\/2017","PTDC\/CTM-CTM\/29869\/2017","UIDB\/04138\/2020","UIDP\/04138\/2020","UIDB\/04567\/2020","UIDP\/04567\/2020","951996","022161"]}]},{"name":"European Union\u2019s Horizon 2020 research and innovation program","award":["PTDC\/QUI-QOR\/32008\/2017","PTDC\/CTM-CTM\/29869\/2017","UIDB\/04138\/2020","UIDP\/04138\/2020","UIDB\/04567\/2020","UIDP\/04567\/2020","951996","022161"],"award-info":[{"award-number":["PTDC\/QUI-QOR\/32008\/2017","PTDC\/CTM-CTM\/29869\/2017","UIDB\/04138\/2020","UIDP\/04138\/2020","UIDB\/04567\/2020","UIDP\/04567\/2020","951996","022161"]}]},{"name":"FEDER through COMPETE 2020, POCI and PORL and FCT through PIDDAC","award":["PTDC\/QUI-QOR\/32008\/2017","PTDC\/CTM-CTM\/29869\/2017","UIDB\/04138\/2020","UIDP\/04138\/2020","UIDB\/04567\/2020","UIDP\/04567\/2020","951996","022161"],"award-info":[{"award-number":["PTDC\/QUI-QOR\/32008\/2017","PTDC\/CTM-CTM\/29869\/2017","UIDB\/04138\/2020","UIDP\/04138\/2020","UIDB\/04567\/2020","UIDP\/04567\/2020","951996","022161"]}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["AppliedChem"],"abstract":"<jats:p>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 (\u00b1)-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.<\/jats:p>","DOI":"10.3390\/appliedchem2030010","type":"journal-article","created":{"date-parts":[[2022,7,12]],"date-time":"2022-07-12T03:50:36Z","timestamp":1657597836000},"page":"142-148","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":0,"title":["Stereoselective Synthesis and Isolation of (\u00b1)-trans,trans-Cyclohexane-1,2,4,5-tetraol"],"prefix":"10.3390","volume":"2","author":[{"given":"Andreia A.","family":"Rosatella","sequence":"first","affiliation":[{"name":"Center for Research in Biosciences & Health Technologies (CBIOS), Universidade Lus\u00f3fona de Humanidades e Tecnologias, Campo Grande 376, 1749-024 Lisboa, Portugal"},{"name":"Research Institute for Medicines (iMed.ULisboa), Faculty of Pharmacy, Universidade de Lisboa, Av. Prof. Gama Pinto, 1649-003 Lisboa, Portugal"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-7284-5948","authenticated-orcid":false,"given":"Carlos A. M.","family":"Afonso","sequence":"additional","affiliation":[{"name":"Research Institute for Medicines (iMed.ULisboa), Faculty of Pharmacy, Universidade de Lisboa, Av. Prof. Gama Pinto, 1649-003 Lisboa, Portugal"}]}],"member":"1968","published-online":{"date-parts":[[2022,7,12]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"7177","DOI":"10.1016\/j.bmc.2008.06.045","article-title":"Synthesis of scyllo-inositol derivatives and their effects on amyloid beta peptide aggregation","volume":"16","author":"Sun","year":"2008","journal-title":"Bioorg. Med. Chem."},{"key":"ref_2","doi-asserted-by":"crossref","first-page":"1450","DOI":"10.1080\/14786419.2012.725397","article-title":"New antimicrobial, mosquito larvicidal and other metabolites from two Artabotrys species","volume":"27","author":"Nyandoro","year":"2013","journal-title":"Nat. Prod. Res."},{"key":"ref_3","first-page":"1819","article-title":"High-yield Production of Optically Active 1,2-Diols from the Corresponding Racemates by Microbial Stereoinversion","volume":"54","author":"Hasegawa","year":"1990","journal-title":"Agric. Biol. Chem. Tokyo"},{"key":"ref_4","doi-asserted-by":"crossref","first-page":"3485","DOI":"10.1016\/j.tet.2010.03.028","article-title":"Stereospecific synthesis of a DL-gala-aminoquercitol derivative","volume":"66","author":"Kurbanoglu","year":"2010","journal-title":"Tetrahedron"},{"key":"ref_5","doi-asserted-by":"crossref","first-page":"249","DOI":"10.2174\/157017807781024273","article-title":"SeO2\/H2O2\/H2O-dioxane: A new catalytic system for trans dihydroxylation of olefins","volume":"4","author":"Gogoi","year":"2007","journal-title":"Lett. Org. Chem."},{"key":"ref_6","doi-asserted-by":"crossref","first-page":"5623","DOI":"10.1002\/anie.200352568","article-title":"Catalytic dihydroxylation of olefins with hydrogen peroxide: An organic-solvent- and metal-free system","volume":"42","author":"Usui","year":"2003","journal-title":"Angew. Chem. Int. Ed."},{"key":"ref_7","doi-asserted-by":"crossref","first-page":"435","DOI":"10.1016\/S0008-6215(98)00073-1","article-title":"One-pot synthesis from 1,4-cyclohexadiene of (+\/\u2212)-1,4\/2,5-cyclohexanetetrol, a naturally occurring cyclitol derivative","volume":"308","author":"Maras","year":"1998","journal-title":"Carbohydr. Res."},{"key":"ref_8","doi-asserted-by":"crossref","first-page":"5920","DOI":"10.1021\/ja502659t","article-title":"Benzannulation via Ruthenium-Catalyzed Diol\u2013Diene [4+2] Cycloaddition: One- and Two-Directional Syntheses of Fluoranthenes and Acenes","volume":"136","author":"Geary","year":"2014","journal-title":"J. Am. Chem. Soc."},{"key":"ref_9","doi-asserted-by":"crossref","first-page":"7545","DOI":"10.1039\/c4cc03983a","article-title":"Ring expansion of cyclic 1,2-diols to form medium sized rings via ruthenium catalyzed transfer hydrogenative [4+2] cycloaddition","volume":"50","author":"Kasun","year":"2014","journal-title":"Chem. Commun."},{"key":"ref_10","doi-asserted-by":"crossref","first-page":"55","DOI":"10.1016\/0957-4166(94)00350-K","article-title":"Highly enantio- and diastereo-selective synthesis of C2-symmetric 3,5-cyclohexadiene-1,2-diol and D2-symmetric cyclohexane-1,2,4,5-tetrol","volume":"6","author":"Suemune","year":"1995","journal-title":"Tetrahedron Asymmetry"},{"key":"ref_11","doi-asserted-by":"crossref","first-page":"894","DOI":"10.1021\/jo01039a002","article-title":"Synthesis of the Five Diastereomeric 1,2,4,5-Cyclohexanetetrols. Nuclear Magnetic Resonance Configurational Proofs1,2","volume":"28","author":"McCasland","year":"1963","journal-title":"J. Org. Chem."},{"key":"ref_12","doi-asserted-by":"crossref","first-page":"985","DOI":"10.1016\/j.tet.2008.11.092","article-title":"Ring opening of epoxides with NaHSO4: Isolation of beta-hydroxy sulfate esters and an effective synthesis for trans-diols","volume":"65","author":"Cavdar","year":"2009","journal-title":"Tetrahedron"},{"key":"ref_13","doi-asserted-by":"crossref","first-page":"1002","DOI":"10.1021\/ed1006772","article-title":"Oxidation of Cyclohexene to trans-1,2-Cyclohexanediol Promoted by p-Toluenesulfonic Acid without Organic Solvents","volume":"88","author":"Rosatella","year":"2011","journal-title":"J. Chem. Educ."},{"key":"ref_14","doi-asserted-by":"crossref","first-page":"2920","DOI":"10.1002\/adsc.201100187","article-title":"Br\u00f8nsted Acid-Catalyzed Dihydroxylation of Olefins in Aqueous Medium","volume":"353","author":"Rosatella","year":"2011","journal-title":"Adv. Synth. Catal."},{"key":"ref_15","doi-asserted-by":"crossref","first-page":"1052","DOI":"10.1002\/hlca.19920750408","article-title":"Catalytic One-Pot Osmylation of Cyclohexadienes: Stereochemical and conformational studies of the resulting polyols","volume":"75","author":"Tschamber","year":"1992","journal-title":"Helv. Chim. Acta"}],"container-title":["AppliedChem"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/2673-9623\/2\/3\/10\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,10]],"date-time":"2025-10-10T23:48:33Z","timestamp":1760140113000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/2673-9623\/2\/3\/10"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2022,7,12]]},"references-count":15,"journal-issue":{"issue":"3","published-online":{"date-parts":[[2022,9]]}},"alternative-id":["appliedchem2030010"],"URL":"https:\/\/doi.org\/10.3390\/appliedchem2030010","relation":{},"ISSN":["2673-9623"],"issn-type":[{"type":"electronic","value":"2673-9623"}],"subject":[],"published":{"date-parts":[[2022,7,12]]}}}