{"id":126,"date":"2021-11-25T15:45:40","date_gmt":"2021-11-25T06:45:40","guid":{"rendered":"http:\/\/achem.okayama-u.ac.jp\/bioorgchem\/WordPress\/?p=126"},"modified":"2021-11-25T15:57:20","modified_gmt":"2021-11-25T06:57:20","slug":"thioureas-as-highly-active-catalysts-for-biomimetic-bromocyclization-of-geranyl-derivatives","status":"publish","type":"post","link":"http:\/\/achem.okayama-u.ac.jp\/bioorgchem\/archives\/126","title":{"rendered":"Thioureas as Highly Active Catalysts for Biomimetic Bromocyclization of Geranyl Derivatives"},"content":{"rendered":"\n<p>Miyuki Terazaki, Kei-ichi Shiomoto, Haruki Mizoguchi, Akira Sakakura*&nbsp;<br><em>Org. Lett.<\/em><strong>2019<\/strong>,&nbsp;<em>21<\/em>&nbsp;(7), 2073\u20132076.&nbsp; (Published online: March&nbsp;&nbsp;12, 2019)&nbsp;<br><a href=\"https:\/\/doi.org\/10.1021\/acs.orglett.9b00352\">DOI: 10.1021\/acs.orglett.9b00352&nbsp;<img decoding=\"async\" src=\"http:\/\/www.cc.okayama-u.ac.jp\/~sakakura\/bioorgchem\/_src\/9514\/img20180629093542651479.png\" alt=\"LinkIcon\"><\/a><\/p>\n\n\n\n<figure class=\"wp-block-image size-full is-resized\"><img loading=\"lazy\" decoding=\"async\" src=\"http:\/\/achem.okayama-u.ac.jp\/bioorgchem\/WordPress\/wp-content\/uploads\/2021\/07\/bromocyclization.png\" alt=\"\" class=\"wp-image-127\" width=\"480\" height=\"152\" srcset=\"http:\/\/achem.okayama-u.ac.jp\/bioorgchem\/WordPress\/wp-content\/uploads\/2021\/07\/bromocyclization.png 960w, http:\/\/achem.okayama-u.ac.jp\/bioorgchem\/WordPress\/wp-content\/uploads\/2021\/07\/bromocyclization-300x95.png 300w, http:\/\/achem.okayama-u.ac.jp\/bioorgchem\/WordPress\/wp-content\/uploads\/2021\/07\/bromocyclization-768x242.png 768w\" sizes=\"auto, (max-width: 480px) 100vw, 480px\" \/><\/figure>\n\n\n\n<p>Thioureas bearing electron-deficient aryl groups show high catalytic activity in the biomimetic bromocyclization of geranyl derivatives. The reaction of geranyl derivatives with&nbsp;<em>N<\/em>-bromosuccinimide (NBS) proceeds rapidly in CH2Cl2 to give the corresponding bromocyclization products in high yields as a ca. 1:1 mixture of endo- and exo-isomers. The reactivity of geranyl derivatives highly depends on the terminal substituent: electron-donating substituents increase the reactivity, while electron-withdrawing substituents decrease the reactivity.<\/p>\n","protected":false},"excerpt":{"rendered":"<p>Miyuki Terazaki, Kei-ichi Shiomoto, Haruki Mizoguchi, Akira Sakakura*&nbsp;Org. Lett.2019,&nbsp;21&nbsp;(7), 2 [&hellip;]<\/p>\n","protected":false},"author":1,"featured_media":127,"comment_status":"closed","ping_status":"closed","sticky":false,"template":"","format":"standard","meta":{"vkexunit_cta_each_option":"","footnotes":""},"categories":[6],"tags":[],"class_list":["post-126","post","type-post","status-publish","format-standard","has-post-thumbnail","hentry","category-publications"],"_links":{"self":[{"href":"http:\/\/achem.okayama-u.ac.jp\/bioorgchem\/wp-json\/wp\/v2\/posts\/126","targetHints":{"allow":["GET"]}}],"collection":[{"href":"http:\/\/achem.okayama-u.ac.jp\/bioorgchem\/wp-json\/wp\/v2\/posts"}],"about":[{"href":"http:\/\/achem.okayama-u.ac.jp\/bioorgchem\/wp-json\/wp\/v2\/types\/post"}],"author":[{"embeddable":true,"href":"http:\/\/achem.okayama-u.ac.jp\/bioorgchem\/wp-json\/wp\/v2\/users\/1"}],"replies":[{"embeddable":true,"href":"http:\/\/achem.okayama-u.ac.jp\/bioorgchem\/wp-json\/wp\/v2\/comments?post=126"}],"version-history":[{"count":2,"href":"http:\/\/achem.okayama-u.ac.jp\/bioorgchem\/wp-json\/wp\/v2\/posts\/126\/revisions"}],"predecessor-version":[{"id":261,"href":"http:\/\/achem.okayama-u.ac.jp\/bioorgchem\/wp-json\/wp\/v2\/posts\/126\/revisions\/261"}],"wp:featuredmedia":[{"embeddable":true,"href":"http:\/\/achem.okayama-u.ac.jp\/bioorgchem\/wp-json\/wp\/v2\/media\/127"}],"wp:attachment":[{"href":"http:\/\/achem.okayama-u.ac.jp\/bioorgchem\/wp-json\/wp\/v2\/media?parent=126"}],"wp:term":[{"taxonomy":"category","embeddable":true,"href":"http:\/\/achem.okayama-u.ac.jp\/bioorgchem\/wp-json\/wp\/v2\/categories?post=126"},{"taxonomy":"post_tag","embeddable":true,"href":"http:\/\/achem.okayama-u.ac.jp\/bioorgchem\/wp-json\/wp\/v2\/tags?post=126"}],"curies":[{"name":"wp","href":"https:\/\/api.w.org\/{rel}","templated":true}]}}