{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,25]],"date-time":"2026-09-25T23:15:21Z","timestamp":1790378121995,"version":"4.1.0"},"reference-count":77,"publisher":"MDPI AG","issue":"1","license":[{"start":{"date-parts":[[2019,12,19]],"date-time":"2019-12-19T00:00:00Z","timestamp":1576713600000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"name":"Economic Development and Innovation Operational Programme","award":["GINOP-2.3.2-15-2016-00014"],"award-info":[{"award-number":["GINOP-2.3.2-15-2016-00014"]}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>A library of 1,2-aminoalcohol derivatives with a neoisopulegol-based octahydrobenzofuran core was developed and applied as chiral catalysts in the addition of diethylzinc to benzaldehyde. The allylic chlorination of (+)-neoisopulegol, derived from natural (\u2013)-isopulegol followed by cyclization, gave the key methyleneoctahydrobenzofuran intermediate. The stereoselective epoxidation of the key intermediate and subsequent oxirane ring opening with primary amines afforded the required 1,2-aminoalcohols. The ring closure of the secondary amine analogues with formaldehyde provided spiro-oxazolidine ring systems. The dihydroxylation of the methylenetetrahydrofuran moiety with OsO4\/NMO (4-methylmorpholine N-oxide) resulted in the formation of a neoisopulegol-based diol in a highly stereoselective reaction. The antimicrobial activity of both the aminoalcohol derivatives and the diol was also explored.<\/jats:p>","DOI":"10.3390\/molecules25010021","type":"journal-article","created":{"date-parts":[[2019,12,23]],"date-time":"2019-12-23T03:23:12Z","timestamp":1577071392000},"page":"21","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":11,"title":["Synthesis and Application of 1,2-Aminoalcohols with Neoisopulegol-Based Octahydrobenzofuran Core"],"prefix":"10.3390","volume":"25","author":[{"given":"Fatima Zahra","family":"Bamou","sequence":"first","affiliation":[{"name":"Institute of Pharmaceutical Chemistry, University of Szeged, Interdisciplinary excellent center, H-6720 Szeged, E\u00f6tv\u00f6s utca 6, Hungary"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-8296-887X","authenticated-orcid":false,"given":"Tam Minh","family":"Le","sequence":"additional","affiliation":[{"name":"Institute of Pharmaceutical Chemistry, University of Szeged, Interdisciplinary excellent center, H-6720 Szeged, E\u00f6tv\u00f6s utca 6, Hungary"},{"name":"MTA-SZTE Stereochemistry Research Group, Hungarian Academy of Sciences, H-6720 Szeged, E\u00f6tv\u00f6s utca 6, Hungary"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Bettina","family":"Volford","sequence":"additional","affiliation":[{"name":"Department of Microbiology, University of Szeged, 6726 Szeged, K\u00f6z\u00e9p fasor 52, Hungary"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-1651-4623","authenticated-orcid":false,"given":"Andr\u00e1s","family":"Szekeres","sequence":"additional","affiliation":[{"name":"Department of Microbiology, University of Szeged, 6726 Szeged, K\u00f6z\u00e9p fasor 52, Hungary"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-2432-8409","authenticated-orcid":false,"given":"Zsolt","family":"Szakonyi","sequence":"additional","affiliation":[{"name":"Institute of Pharmaceutical Chemistry, University of Szeged, Interdisciplinary excellent center, H-6720 Szeged, E\u00f6tv\u00f6s utca 6, Hungary"},{"name":"Interdisciplinary Centre of Natural Products, University of Szeged, H-6720 Szeged, E\u00f6tv\u00f6s utca 6, Hungary"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"1968","published-online":{"date-parts":[[2019,12,19]]},"reference":[{"key":"ref_1","first-page":"571","article-title":"Furans and their benzo derivatives: Applications","volume":"Volume 5","author":"Katritzky","year":"2008","journal-title":"Comprehensive Heterocyclic Chemistry III"},{"key":"ref_2","first-page":"395","article-title":"Furans and their benzo derivatives: Applications","volume":"Volume 2","author":"Katritzky","year":"1996","journal-title":"Comprehensive Heterocyclic Chemistry II"},{"key":"ref_3","doi-asserted-by":"crossref","first-page":"199","DOI":"10.1038\/nchembio.302","article-title":"Domino access to highly substituted chromans and isochromans from carbohydrates","volume":"6","author":"Leibeling","year":"2010","journal-title":"Nat. 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