{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,1,20]],"date-time":"2026-01-20T12:33:58Z","timestamp":1768912438082,"version":"3.49.0"},"reference-count":34,"publisher":"MDPI AG","issue":"23","license":[{"start":{"date-parts":[[2024,11,29]],"date-time":"2024-11-29T00:00:00Z","timestamp":1732838400000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"name":"MUR (Ministero dell\u2019Universit\u00e0 e della Ricerca)"},{"name":"PON R&amp;I 2014-2020-Asse IV \u201cIstruzione e Ricerca per il recupero-REACT-EU,\u201d Azione IV.6 \u201cContratti di Ricerca su tematiche Green\u201d"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["IJMS"],"abstract":"<jats:p>The 1,3-dithiolane ring has been recently rehabilitated as a chemical scaffold in drug design. However, for derivatives that are substituted in position 4, the introduction of a chiral center on the heterocycle demands the separation and characterization of the stereoisomers. We report the first chiral resolution and absolute configuration (AC) assignment for (1,4-dithiaspiro[4.5]decan-2-yl)methanol (R\/S)-1, a key synthon for dithiolane-based biologically active compounds. Using (semi)preparative enantioselective HPLC, we isolated enantiomeric 1. The AC was assigned by using (+)-1 for the enantioselective synthesis of (+)-BS148, a sigma receptor modulator. An X-ray diffraction analysis established the (R)-configuration of (+)-BS148 and, by extension, of (+)-1. This method provides a reliable approach for preparing enantiopure 1,3-dithiolane scaffolds and establishes reference standards for AC determination of related compounds.<\/jats:p>","DOI":"10.3390\/ijms252312880","type":"journal-article","created":{"date-parts":[[2024,12,2]],"date-time":"2024-12-02T03:50:57Z","timestamp":1733111457000},"page":"12880","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":1,"title":["1,3-Dithiolane as a Privileged Scaffold in Bioactive Derivatives: Chiral Resolution and Assignment of Absolute Configuration"],"prefix":"10.3390","volume":"25","author":[{"given":"Roberta","family":"Listro","sequence":"first","affiliation":[{"name":"Department of Drug Sciences, University of Pavia, Viale Taramelli 12, 27100 Pavia, Italy"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-1008-5736","authenticated-orcid":false,"given":"Giacomo","family":"Rossino","sequence":"additional","affiliation":[{"name":"Department of Drug Sciences, University of Pavia, Viale Taramelli 12, 27100 Pavia, Italy"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-9759-5148","authenticated-orcid":false,"given":"Valeria","family":"Cavalloro","sequence":"additional","affiliation":[{"name":"Department of Earth and Environmental Sciences, University of Pavia, Via Sant\u2019Epifanio 14, 27100 Pavia, Italy"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-2458-3728","authenticated-orcid":false,"given":"Daniela","family":"Rossi","sequence":"additional","affiliation":[{"name":"Department of Drug Sciences, University of Pavia, Viale Taramelli 12, 27100 Pavia, Italy"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-4991-145X","authenticated-orcid":false,"given":"Massimo","family":"Boiocchi","sequence":"additional","affiliation":[{"name":"Centro Grandi Strumenti, University of Pavia, Via Bassi 21, 27100 Pavia, Italy"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-0914-5356","authenticated-orcid":false,"given":"Marina Simona","family":"Robescu","sequence":"additional","affiliation":[{"name":"Department of Drug Sciences, University of Pavia, Viale Taramelli 12, 27100 Pavia, Italy"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-1286-2535","authenticated-orcid":false,"given":"Teodora","family":"Bavaro","sequence":"additional","affiliation":[{"name":"Department of Drug Sciences, University of Pavia, Viale Taramelli 12, 27100 Pavia, Italy"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-6320-9712","authenticated-orcid":false,"given":"Silvia","family":"Franchini","sequence":"additional","affiliation":[{"name":"Department of Life Sciences, University of Modena and Reggio Emilia, Via Campi 103, 41125 Modena, Italy"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-6916-4933","authenticated-orcid":false,"given":"Claudia","family":"Sorbi","sequence":"additional","affiliation":[{"name":"Department of Life Sciences, University of Modena and Reggio Emilia, Via Campi 103, 41125 Modena, Italy"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-0236-0662","authenticated-orcid":false,"given":"Marco","family":"De Amici","sequence":"additional","affiliation":[{"name":"Department of Pharmaceutical Sciences, University of Milan, Via Luigi Mangiagalli 25, 20133 Milan, Italy"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-0382-7479","authenticated-orcid":false,"given":"Pasquale","family":"Linciano","sequence":"additional","affiliation":[{"name":"Department of Drug Sciences, University of Pavia, Viale Taramelli 12, 27100 Pavia, Italy"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-2954-7558","authenticated-orcid":false,"given":"Simona","family":"Collina","sequence":"additional","affiliation":[{"name":"Department of Drug Sciences, University of Pavia, Viale Taramelli 12, 27100 Pavia, Italy"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"1968","published-online":{"date-parts":[[2024,11,29]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"2727","DOI":"10.1016\/S0960-894X(00)00553-9","article-title":"Benzylidene ketal derivatives as M2 muscarinic receptor antagonists","volume":"24","author":"Boyle","year":"2000","journal-title":"Bioorg. 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