{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,10,17]],"date-time":"2025-10-17T13:38:13Z","timestamp":1760708293686},"reference-count":41,"publisher":"Wiley","issue":"7","license":[{"start":{"date-parts":[[2011,4,15]],"date-time":"2011-04-15T00:00:00Z","timestamp":1302825600000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Chirality"],"published-print":{"date-parts":[[2011,8]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>An efficient methodology for the preparation of the \u03b1\u2010tetrasubstituted proline analog (<jats:italic>S<\/jats:italic>,<jats:italic>S<\/jats:italic>,<jats:italic>S<\/jats:italic>)\u20102\u2010methyloctahydroindole\u20102\u2010carboxylic acid, (<jats:italic>S<\/jats:italic>,<jats:italic>S<\/jats:italic>,<jats:italic>S<\/jats:italic>)\u2010(\u03b1Me)Oic, and its enantiomer, (<jats:italic>R<\/jats:italic>,<jats:italic>R<\/jats:italic>,<jats:italic>R<\/jats:italic>)\u2010(\u03b1Me)Oic, has been developed. Starting from easily available substrates and through simple transformations, a racemic precursor has been synthesized in excellent yield and further subjected to HPLC resolution using a cellulose\u2010derived chiral stationary phase. Specifically, a semipreparative (250 mm \u00d7 20 mm ID) Chiralpak\u00ae IC column has allowed the efficient resolution of more than 4 g of racemate using a mixture of <jats:italic>n<\/jats:italic>\u2010hexane\/<jats:italic>tert<\/jats:italic>\u2010butyl methyl ether\/2\u2010propanol as the eluent. Multigram quantities of the target amino acids have been isolated in enantiomerically pure form and suitably protected for incorporation into peptides. Chirality, 2011. \u00a9 2011 Wiley\u2010Liss, Inc.<\/jats:p>","DOI":"10.1002\/chir.20952","type":"journal-article","created":{"date-parts":[[2011,4,16]],"date-time":"2011-04-16T04:10:00Z","timestamp":1302927000000},"page":"507-513","source":"Crossref","is-referenced-by-count":17,"title":["Practical access to the proline analogs (<i>S<\/i>,<i>S<\/i>,<i>S<\/i>)\u2010 and (<i>R<\/i>,<i>R<\/i>,<i>R<\/i>)\u20102\u2010methyloctahydroindole\u20102\u2010carboxylic acids by HPLC enantioseparation"],"prefix":"10.1002","volume":"23","author":[{"given":"Francisco J.","family":"Sayago","sequence":"first","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Mar\u00eda J.","family":"Pueyo","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"M. 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