{"id":81495,"date":"2025-06-15T16:05:23","date_gmt":"2025-06-15T07:05:23","guid":{"rendered":"https:\/\/www.waseda.jp\/inst\/research\/?p=81495"},"modified":"2025-07-15T16:18:07","modified_gmt":"2025-07-15T07:18:07","slug":"facile-generation-of-ortho-quinodimethanes-toward-polycyclic-compounds%ef%bc%88published-in-chem-june-2025%ef%bc%89","status":"publish","type":"post","link":"https:\/\/www.waseda.jp\/inst\/research\/news\/81495","title":{"rendered":"Facile generation of ortho-quinodimethanes toward polycyclic compounds\uff08Published in Chem, June, 2025\uff09"},"content":{"rendered":"\n\n\n\n\n\n\n\n\n
Journal Title
\n\/\u63b2\u8f09\u30b8\u30e3\u30fc\u30ca\u30eb\u540d<\/td>\n		Chem<\/td>\n<\/tr>\n
Publication Year and Month
\n\/\u63b2\u8f09\u5e74\u6708<\/td>\n		June, 2025<\/td>\n<\/tr>\n
Paper Title
\n\/\u8ad6\u6587\u30bf\u30a4\u30c8\u30eb<\/td>\n		Facile generation of ortho-quinodimethanes toward polycyclic compounds<\/td>\n<\/tr>\n
DOI
\n\/\u8ad6\u6587DOI<\/td>\n		10.1016\/j.chempr.2025.102615<\/a><\/td>\n<\/tr>\n
\u00a0Author of Waseda University
\n\/\u672c\u5b66\u306e\u8457\u8005<\/td>\n		INAGAKI, Kazuya(Student, Faculty of Science and Engineering, School of Advanced Science and Engineering):Lead Author<\/span><\/td>\n<\/tr>\n
Related Websites
\n\/\u95a2\u9023Web<\/td>\n		–<\/td>\n<\/tr>\n
Abstract
\n\/\u6284\u9332<\/td>\n		The streamlined synthesis of complex and functional molecules from simple and readily available starting materials has long been a fundamental goal in organic synthesis. Polycyclic carbon skeletons are particularly attractive molecular frameworks as they are prevalent in terpenoids and pharmaceuticals. Among the various strategies and reactions to access these structures,1<\/sup><\/a><\/span>\u00a0Diels-Alder reaction2<\/sup><\/a><\/span>\u00a0stands out as one of the most powerful tools, facilitating the [4+2] cycloaddition between a diene and a dienophile to rapidly form six-membered rings. Its ability to create complex cyclic structures with high regio- and stereoselectivity makes it indispensable in synthesizing natural products and bioactive compounds. Various dienes and dienophiles are known, and reaction development that leverages their exceptional reactivity is ongoing.3<\/sup><\/a><\/span>,<\/sup>4<\/sup><\/a><\/span>,<\/sup>5<\/sup><\/a><\/span>,<\/sup>6<\/sup><\/a><\/span>\u00a0Among these,\u00a0ortho<\/i>-quinodimethane (o<\/i>QDM) has long been recognized as an outstanding diene (Figure 1<\/a>A).7<\/sup><\/a><\/span>,<\/sup>8<\/sup><\/a><\/span>,<\/sup>9<\/sup><\/a><\/span>\u00a0This unique reactivity allows for the efficient construction of benzo-fused polycyclic skeletons, which are prevalent in biologically important molecules.10<\/sup><\/a><\/span>,<\/sup>11<\/sup><\/a><\/span>,<\/sup>12<\/sup><\/a><\/span>,<\/sup>13<\/sup><\/a><\/span>,<\/sup>14<\/sup><\/a><\/span>\u00a0However,\u00a0o<\/i>QDM\u2019s high reactivity can only be unlocked by\u00a0in situ<\/i>\u00a0generation from precursors (e.g., benzocyclobutenes and benzoheteroles) under harsh conditions.7<\/sup><\/a><\/span>,<\/sup>8<\/sup><\/a><\/span>,<\/sup>9<\/sup><\/a><\/span>,<\/sup>15<\/sup><\/a><\/span>,<\/sup>16<\/sup><\/a><\/span>\u00a0Furthermore, preparing these precursors is often laborious and also limits product diversity, which is a recurring issue in synthetic chemistry. A novel approach to generating\u00a0o<\/i>QDM from simple, readily available chemicals could address these challenges, enabling a diversity-oriented synthesis of polycyclic compounds in short sequence.17<\/sup><\/a><\/span>,<\/sup>18<\/sup><\/a><\/span>,<\/sup>19<\/sup><\/a><\/span>,<\/sup>20<\/sup><\/a><\/span>\u00a0Despite extensive studies on catalytic methodologies,21<\/sup><\/a><\/span>,<\/sup>22<\/sup><\/a><\/span>,<\/sup>23<\/sup><\/a><\/span>,<\/sup>24<\/sup><\/a><\/span>,<\/sup>25<\/sup><\/a><\/span>\u00a0these challenges have persisted for nearly 70 years since\u00a0o<\/i>QDM was first reported by Cava.26<\/sup><\/a><\/span>,<\/sup>27<\/sup><\/a><\/span><\/td>\n<\/tr>\n<\/tbody>\n<\/table>\n","protected":false},"excerpt":{"rendered":"

Journal Title \/\u63b2\u8f09\u30b8\u30e3\u30fc\u30ca\u30eb\u540d Chem Publication Year and Month \/\u63b2\u8f09\u5e74\u6708 June, 2025 Paper Title \/\u8ad6\u6587\u30bf\u30a4\u30c8\u30eb Facile generation […]<\/p>\n","protected":false},"author":3,"featured_media":0,"comment_status":"closed","ping_status":"closed","sticky":false,"template":"","format":"standard","meta":{"_acf_changed":false,"footnotes":""},"categories":[],"tags":[218,217],"class_list":["post-81495","post","type-post","status-publish","format-standard","hentry","tag-impact-en","tag-impact"],"acf":[],"_links":{"self":[{"href":"https:\/\/www.waseda.jp\/inst\/research\/wp-json\/wp\/v2\/posts\/81495","targetHints":{"allow":["GET"]}}],"collection":[{"href":"https:\/\/www.waseda.jp\/inst\/research\/wp-json\/wp\/v2\/posts"}],"about":[{"href":"https:\/\/www.waseda.jp\/inst\/research\/wp-json\/wp\/v2\/types\/post"}],"author":[{"embeddable":true,"href":"https:\/\/www.waseda.jp\/inst\/research\/wp-json\/wp\/v2\/users\/3"}],"replies":[{"embeddable":true,"href":"https:\/\/www.waseda.jp\/inst\/research\/wp-json\/wp\/v2\/comments?post=81495"}],"version-history":[{"count":2,"href":"https:\/\/www.waseda.jp\/inst\/research\/wp-json\/wp\/v2\/posts\/81495\/revisions"}],"predecessor-version":[{"id":81501,"href":"https:\/\/www.waseda.jp\/inst\/research\/wp-json\/wp\/v2\/posts\/81495\/revisions\/81501"}],"wp:attachment":[{"href":"https:\/\/www.waseda.jp\/inst\/research\/wp-json\/wp\/v2\/media?parent=81495"}],"wp:term":[{"taxonomy":"category","embeddable":true,"href":"https:\/\/www.waseda.jp\/inst\/research\/wp-json\/wp\/v2\/categories?post=81495"},{"taxonomy":"post_tag","embeddable":true,"href":"https:\/\/www.waseda.jp\/inst\/research\/wp-json\/wp\/v2\/tags?post=81495"}],"curies":[{"name":"wp","href":"https:\/\/api.w.org\/{rel}","templated":true}]}}