{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,2]],"date-time":"2026-10-02T20:39:28Z","timestamp":1790973568538,"version":"4.1.0"},"reference-count":62,"publisher":"Wiley","issue":"5","license":[{"start":{"date-parts":[[2007,11,23]],"date-time":"2007-11-23T00:00:00Z","timestamp":1195776000000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Chemistry A European J"],"published-print":{"date-parts":[[2008,2,8]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>A novel enantioselective total synthesis of the oral contraceptive desogestrel (<jats:bold>2<\/jats:bold>) is described, in which the tetracyclic steroid core is formed by a sequence of two consecutive Heck reactions. Conversion of the known enantiopure diketone <jats:bold>7<\/jats:bold> led to the chiral bicycle <jats:bold>6<\/jats:bold> which was used for a diastereoselective intermolecular Heck reaction with vinyliodide <jats:bold>5<\/jats:bold> to give <jats:bold>15<\/jats:bold>. In the following intramolecular Heck reaction, the tetracyclic ring system was formed to give <jats:bold>4<\/jats:bold>, from which the synthesis of desogestrel (<jats:bold>2<\/jats:bold>) was furnished.<\/jats:p>","DOI":"10.1002\/chem.200700182","type":"journal-article","created":{"date-parts":[[2007,11,23]],"date-time":"2007-11-23T10:17:26Z","timestamp":1195813046000},"page":"1541-1551","source":"Crossref","is-referenced-by-count":22,"title":["Enantioselective Total Synthesis of the Oral Contraceptive Desogestrel by a Double Heck Reaction"],"prefix":"10.1002","volume":"14","author":[{"given":"Lutz\u2005F.","family":"Tietze","sequence":"first","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Ilga\u2005K.","family":"Krimmelbein","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2008,2]]},"reference":[{"key":"e_1_2_6_1_2","unstructured":"\u00a0"},{"key":"e_1_2_6_2_2","first-page":"712","volume":"39","author":"Karck U.","year":"2006","journal-title":"Gynaecologia"},{"key":"e_1_2_6_3_2","doi-asserted-by":"publisher","DOI":"10.2217\/17455057.2.3.351"},{"key":"e_1_2_6_4_2","first-page":"181","volume":"1","author":"Newton J.","year":"2003","journal-title":"J. Drug Eval."},{"key":"e_1_2_6_5_2","doi-asserted-by":"publisher","DOI":"10.1592\/phco.23.15.1573.31950"},{"key":"e_1_2_6_6_2","doi-asserted-by":"publisher","DOI":"10.1345\/aph.10149"},{"key":"e_1_2_6_7_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0960-0760(01)00124-8"},{"key":"e_1_2_6_8_2","doi-asserted-by":"publisher","DOI":"10.1002\/recl.19931121204"},{"key":"e_1_2_6_9_2","unstructured":"Examples for recent reviews on the Heck reaction:"},{"key":"e_1_2_6_10_2","doi-asserted-by":"publisher","DOI":"10.1002\/9783527619405.ch2m"},{"key":"e_1_2_6_11_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr9903048"},{"key":"e_1_2_6_12_2","volume-title":"Metal\u2010Catalyzed Cross Coupling Reactions","author":"Meijere A. de","year":"1998"},{"key":"e_1_2_6_13_2","volume-title":"Metal\u2010Catalyzed Cross Coupling Reactions","author":"Link J. T.","year":"1998"},{"key":"e_1_2_6_14_2","unstructured":"Examples for recent reviews on the asymmetric Heck reaction:"},{"key":"e_1_2_6_15_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr030700x"},{"key":"e_1_2_6_16_2","doi-asserted-by":"publisher","DOI":"10.1002\/adsc.200404203"},{"key":"e_1_2_6_17_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr020039h"},{"key":"e_1_2_6_18_2","doi-asserted-by":"publisher","DOI":"10.1002\/0471212466.ch51"},{"key":"e_1_2_6_19_2","doi-asserted-by":"publisher","DOI":"10.1002\/0471721506.ch21"},{"key":"e_1_2_6_20_2","first-page":"457","volume-title":"in Comprehensive Asymmetric Catalysis I\u2013III, Vol. 1","author":"Shibasaki M.","year":"1999"},{"key":"e_1_2_6_21_2","unstructured":"\u00a0"},{"key":"e_1_2_6_22_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.19961081922"},{"key":"e_1_2_6_22_3","doi-asserted-by":"publisher","DOI":"10.1002\/anie.199622591"},{"key":"e_1_2_6_23_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja981539o"},{"key":"e_1_2_6_24_2","unstructured":"\u00a0"},{"key":"e_1_2_6_25_2","doi-asserted-by":"publisher","DOI":"10.1002\/(SICI)1099-0690(200005)2000:9<1827::AID-EJOC1827>3.0.CO;2-V"},{"key":"e_1_2_6_26_2","doi-asserted-by":"publisher","DOI":"10.1002\/1099-0690(200105)2001:9<1619::AID-EJOC1619>3.0.CO;2-T"},{"key":"e_1_2_6_27_2","doi-asserted-by":"publisher","DOI":"10.3998\/ark.5550190.0008.517"},{"key":"e_1_2_6_28_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200601003"},{"key":"e_1_2_6_28_3","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200601003"},{"key":"e_1_2_6_29_2","unstructured":"\u00a0"},{"key":"e_1_2_6_30_2","doi-asserted-by":"crossref","first-page":"560","DOI":"10.1055\/s-2001-12438","author":"Tietze L. F.","year":"2001","journal-title":"Synlett"},{"key":"e_1_2_6_31_2","doi-asserted-by":"publisher","DOI":"10.1002\/1521-3765(20020503)8:9<2116::AID-CHEM2116>3.0.CO;2-4"},{"key":"e_1_2_6_32_2","unstructured":"\u00a0"},{"key":"e_1_2_6_33_2","doi-asserted-by":"publisher","DOI":"10.1002\/recl.19750940203"},{"key":"e_1_2_6_34_2","doi-asserted-by":"publisher","DOI":"10.1002\/recl.19881070406"},{"key":"e_1_2_6_35_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4020(01)89263-2"},{"key":"e_1_2_6_36_2","doi-asserted-by":"publisher","DOI":"10.1080\/00304949709355234"},{"key":"e_1_2_6_37_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja983179a"},{"key":"e_1_2_6_38_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja048808x"},{"key":"e_1_2_6_39_2","unstructured":"\u00a0"},{"key":"e_1_2_6_40_2","unstructured":"A.\u2005J. van\u2005denBroek(Akzo N.V.) DE 2361120 1974;"},{"key":"e_1_2_6_41_2","unstructured":"S.Ring G.Teichm\u00fcller S.Schwarz B.Erhart B.Undeutsch H.Raethe P.Moellmann C.Pfeiffer H.\u2010J.Palme(Jenapharm GmbH) US 5831104 1998;"},{"key":"e_1_2_6_42_2","unstructured":"P.Grisenti F.Pecora E.Verza M.Leoni L.Bossi(Poli Industria Chimica Spa) WO 2004014934 2004;"},{"key":"e_1_2_6_43_2","unstructured":"J.Li N.Zhao X.Zhang L.Ma(Shanghai Desano Pharmaceutical Development Co. Ltd.) CN 1865276 2006."},{"key":"e_1_2_6_44_2","unstructured":"\u00a0"},{"key":"e_1_2_6_45_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo00894a003"},{"key":"e_1_2_6_46_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo00925a002"},{"key":"e_1_2_6_47_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo00925a003"},{"key":"e_1_2_6_48_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.19710831307"},{"key":"e_1_2_6_48_3","doi-asserted-by":"publisher","DOI":"10.1002\/anie.197104961"},{"key":"e_1_2_6_49_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo00031a005"},{"key":"e_1_2_6_50_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo00270a011"},{"key":"e_1_2_6_51_2","unstructured":"\u00a0"},{"key":"e_1_2_6_52_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.19951071708"},{"key":"e_1_2_6_52_3","doi-asserted-by":"publisher","DOI":"10.1002\/anie.199518441"},{"key":"e_1_2_6_53_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.19951071709"},{"key":"e_1_2_6_53_3","doi-asserted-by":"publisher","DOI":"10.1002\/anie.199518481"},{"key":"e_1_2_6_54_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.19970030823"},{"key":"e_1_2_6_55_2","unstructured":"N.Cohen(Hoffman\u2010La Roche) DE 2349260 1974."},{"key":"e_1_2_6_56_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0039-128X(97)00006-8"},{"key":"e_1_2_6_57_2","unstructured":"K.Ponsold H.Kasch Patent (VEB Jenapharm) DE 2523179 1976."}],"container-title":["Chemistry \u2013 A European Journal"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/api.wiley.com\/onlinelibrary\/tdm\/v1\/articles\/10.1002%2Fchem.200700182","content-type":"unspecified","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/chem.200700182","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,12]],"date-time":"2025-10-12T12:52:21Z","timestamp":1760273541000},"score":1,"resource":{"primary":{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/10.1002\/chem.200700182"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2008,2]]},"references-count":62,"journal-issue":{"issue":"5","published-print":{"date-parts":[[2008,2,8]]}},"alternative-id":["10.1002\/chem.200700182"],"URL":"https:\/\/doi.org\/10.1002\/chem.200700182","archive":["Portico"],"relation":{},"ISSN":["0947-6539","1521-3765"],"issn-type":[{"value":"0947-6539","type":"print"},{"value":"1521-3765","type":"electronic"}],"subject":[],"published":{"date-parts":[[2008,2]]}}}