{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,23]],"date-time":"2026-09-23T15:00:43Z","timestamp":1790175643146,"version":"4.1.0"},"reference-count":24,"publisher":"Wiley","issue":"9","license":[{"start":{"date-parts":[[2005,2,28]],"date-time":"2005-02-28T00:00:00Z","timestamp":1109548800000},"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":[[2005,4,22]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>The natural products <jats:italic>cis<\/jats:italic>\u2010<jats:italic>p<\/jats:italic>\u2010menthane\u20101,7\u2010diol (<jats:italic>cis<\/jats:italic>\u2010<jats:bold>IV<\/jats:bold>), <jats:italic>cis<\/jats:italic>\u2010<jats:italic>p<\/jats:italic>\u2010menth\u20108\u2010ene\u20101,7\u2010diol (<jats:italic>cis<\/jats:italic>\u2010<jats:bold>I<\/jats:bold>) and <jats:italic>cis<\/jats:italic>\u2010<jats:italic>p<\/jats:italic>\u2010menthane\u20101,7,8\u2010triol (<jats:italic>cis<\/jats:italic>\u2010<jats:bold>II<\/jats:bold>) are obtained starting from the corresponding <jats:italic>cis<\/jats:italic>\u2010cyanohydrins, <jats:italic>cis<\/jats:italic>\u2010<jats:bold>2<\/jats:bold> and <jats:italic>cis<\/jats:italic>\u2010<jats:bold>7<\/jats:bold>, respectively, by chemical transformation of the cyano into the hydroxymethyl group. The key step of the synthesis is the very high <jats:italic>cis<\/jats:italic>\u2010selectivity (\u2265 96\u2009%) of the MeHNL\u2010catalyzed HCN addition to 4\u2010alkylcyclohexanones. From 4\u2010isopropylcyclohexanone (<jats:bold>1<\/jats:bold>) the cyanohydrin <jats:italic>cis<\/jats:italic>\u2010<jats:bold>2<\/jats:bold> and from 4\u2010(1\u2010methylvinyl)cyclohexanone (<jats:bold>6<\/jats:bold>) the cyanohydrin <jats:italic>cis<\/jats:italic>\u2010<jats:bold>7<\/jats:bold> result almost quantitatively. Regioselective hydroxylation of <jats:italic>cis<\/jats:italic>\u2010<jats:bold>I<\/jats:bold> affords the triol <jats:italic>cis<\/jats:italic>\u2010<jats:bold>II<\/jats:bold>. X\u2010ray crystal structure determinations of the final products confirm their <jats:italic>cis<\/jats:italic>\u2010configuration.<\/jats:p>","DOI":"10.1002\/chem.200401147","type":"journal-article","created":{"date-parts":[[2005,2,28]],"date-time":"2005-02-28T07:17:19Z","timestamp":1109575039000},"page":"2783-2787","source":"Crossref","is-referenced-by-count":8,"title":["Stereoselective Synthesis of <i>cis<\/i>\u2010<i>p<\/i>\u2010Menth\u20108\u2010ene\u20101,7\u2010diol, <i>cis<\/i>\u2010<i>p<\/i>\u2010Menthane\u20101,7\u2010diol, and <i>cis<\/i>\u2010<i>p<\/i>\u2010Menthane\u20101,7,8\u2010triol"],"prefix":"10.1002","volume":"11","author":[{"given":"Christoph","family":"Kobler","sequence":"first","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Franz","family":"Effenberger","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2005,4,15]]},"reference":[{"key":"e_1_2_6_1_2","doi-asserted-by":"publisher","DOI":"10.1021\/np50086a013"},{"key":"e_1_2_6_2_2","doi-asserted-by":"publisher","DOI":"10.1248\/cpb.46.1603"},{"key":"e_1_2_6_3_2","doi-asserted-by":"publisher","DOI":"10.3109\/00498258709043961"},{"key":"e_1_2_6_4_2","unstructured":"\u00a0"},{"key":"e_1_2_6_5_2","doi-asserted-by":"publisher","DOI":"10.1071\/CH9960741"},{"key":"e_1_2_6_6_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0959-8049(99)00036-2"},{"key":"e_1_2_6_7_2","doi-asserted-by":"publisher","DOI":"10.1071\/CH9931869"},{"key":"e_1_2_6_8_2","doi-asserted-by":"publisher","DOI":"10.1271\/bbb1961.41.435"},{"key":"e_1_2_6_9_2","unstructured":"\u00a0"},{"key":"e_1_2_6_10_2","doi-asserted-by":"publisher","DOI":"10.1002\/1521-3757(20020603)114:11<1957::AID-ANGE1957>3.0.CO;2-#"},{"key":"e_1_2_6_10_3","doi-asserted-by":"publisher","DOI":"10.1002\/1521-3773(20020603)41:11<1876::AID-ANIE1876>3.0.CO;2-1"},{"key":"e_1_2_6_11_2","doi-asserted-by":"publisher","DOI":"10.1139\/v02-087"},{"key":"e_1_2_6_12_2","unstructured":"\u00a0"},{"key":"e_1_2_6_13_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja00412a024"},{"key":"e_1_2_6_14_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo00205a015"},{"key":"e_1_2_6_15_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(01)85493-9"},{"key":"e_1_2_6_16_2","unstructured":"CCDC\u2010250608\u2013CCDC\u2010250610 and CCDC\u2010174989 contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk\/data_request\/cif."},{"key":"e_1_2_6_17_2","first-page":"976","volume":"46","author":"Brussee J.","year":"1990","journal-title":"Tetrahedron"},{"key":"e_1_2_6_18_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0957-4166(99)00280-3"},{"key":"e_1_2_6_19_2","unstructured":"\u00a0"},{"key":"e_1_2_6_20_2","first-page":"1842","volume":"35","author":"Brown H. C.","year":"1970","journal-title":"J. Org. 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