{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,10,12]],"date-time":"2025-10-12T19:32:18Z","timestamp":1760297538362},"reference-count":20,"publisher":"Wiley","issue":"9","license":[{"start":{"date-parts":[[2005,9,23]],"date-time":"2005-09-23T00:00:00Z","timestamp":1127433600000},"content-version":"vor","delay-in-days":22,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Helvetica Chimica Acta"],"published-print":{"date-parts":[[2005,9]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>Two new <jats:italic>\u03c9<\/jats:italic>\u2010(1<jats:italic>H<\/jats:italic>\u2010pyrrol\u20103\u2010yl)alkanoic acids <jats:bold>8a<\/jats:bold>,<jats:bold>b<\/jats:bold> and the corresponding amines <jats:bold>9a<\/jats:bold>,<jats:bold>b<\/jats:bold> were prepared on large scale in 41\u201351 and 27\u201339% overall yield, respectively, starting from <jats:italic>N<\/jats:italic>\u2010phenylsulfonyl\u2010protected pyrrole. The target compounds contain the desired functional groups for attachment of biomolecules such as proteins. During synthesis, an unprecedented partial reduction of the pyrrole ring with NaBH<jats:sub>3<\/jats:sub>CN in glacial AcOH was observed, for which a plausible mechanism is proposed (<jats:italic>Scheme\u20053<\/jats:italic>).<\/jats:p>","DOI":"10.1002\/hlca.200590183","type":"journal-article","created":{"date-parts":[[2005,9,23]],"date-time":"2005-09-23T08:48:03Z","timestamp":1127465283000},"page":"2470-2478","source":"Crossref","is-referenced-by-count":15,"title":["Synthesis of Long\u2010Chain 3\u2010Alkylpyrroles Bearing Terminal Carboxy or Amino Groups"],"prefix":"10.1002","volume":"88","author":[{"given":"Jos\u00e9\u2005M.","family":"Freitas","sequence":"first","affiliation":[]},{"given":"Lu\u00edsa\u2005M.","family":"Abrantes","sequence":"additional","affiliation":[]},{"given":"Tamis","family":"Darbre","sequence":"additional","affiliation":[]}],"member":"311","published-online":{"date-parts":[[2005,9,23]]},"reference":[{"key":"e_1_2_1_1_2","doi-asserted-by":"publisher","DOI":"10.1039\/f19868201259"},{"key":"e_1_2_1_1_3","doi-asserted-by":"publisher","DOI":"10.1021\/ja00098a053"},{"key":"e_1_2_1_1_4","doi-asserted-by":"publisher","DOI":"10.1021\/ja964261d"},{"key":"e_1_2_1_1_5","doi-asserted-by":"publisher","DOI":"10.1051\/analusis:1999270558"},{"key":"e_1_2_1_1_6","doi-asserted-by":"publisher","DOI":"10.1385\/ABAB:89:2-3:127"},{"key":"e_1_2_1_1_7","doi-asserted-by":"publisher","DOI":"10.1016\/S0956-5663(01)00133-6"},{"key":"e_1_2_1_1_8","doi-asserted-by":"publisher","DOI":"10.1016\/S0379-6779(00)01230-3"},{"key":"e_1_2_1_2_2","first-page":"233","volume":"15","author":"Delabouglise D.","year":"1991","journal-title":"New J. Chem."},{"key":"e_1_2_1_3_2","doi-asserted-by":"publisher","DOI":"10.15227\/orgsyn.038.0055"},{"key":"e_1_2_1_3_3","doi-asserted-by":"publisher","DOI":"10.1080\/00397918708057756"},{"key":"e_1_2_1_4_2","doi-asserted-by":"publisher","DOI":"10.1080\/00397917908066715"},{"key":"e_1_2_1_5_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo9823339"},{"key":"e_1_2_1_6_2","doi-asserted-by":"publisher","DOI":"10.1139\/v77-583"},{"key":"e_1_2_1_6_3","doi-asserted-by":"publisher","DOI":"10.1021\/jo01304a006"},{"key":"e_1_2_1_6_4","doi-asserted-by":"publisher","DOI":"10.1246\/bcsj.56.280"},{"key":"e_1_2_1_7_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo00167a014"},{"key":"e_1_2_1_8_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0928-4931(01)00209-0"},{"key":"e_1_2_1_9_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo00278a035"},{"key":"e_1_2_1_10_2","doi-asserted-by":"publisher","DOI":"10.1021\/jm00050a012"},{"key":"e_1_2_1_11_2","doi-asserted-by":"publisher","DOI":"10.1055\/s-1981-29473"}],"container-title":["Helvetica Chimica Acta"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/api.wiley.com\/onlinelibrary\/tdm\/v1\/articles\/10.1002%2Fhlca.200590183","content-type":"unspecified","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/hlca.200590183","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2023,10,18]],"date-time":"2023-10-18T01:25:34Z","timestamp":1697592334000},"score":1,"resource":{"primary":{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/10.1002\/hlca.200590183"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2005,9]]},"references-count":20,"journal-issue":{"issue":"9","published-print":{"date-parts":[[2005,9]]}},"alternative-id":["10.1002\/hlca.200590183"],"URL":"https:\/\/doi.org\/10.1002\/hlca.200590183","archive":["Portico"],"relation":{},"ISSN":["0018-019X","1522-2675"],"issn-type":[{"value":"0018-019X","type":"print"},{"value":"1522-2675","type":"electronic"}],"subject":[],"published":{"date-parts":[[2005,9]]}}}