{"id":147,"date":"2021-11-25T15:44:20","date_gmt":"2021-11-25T06:44:20","guid":{"rendered":"http:\/\/achem.okayama-u.ac.jp\/bioorgchem\/WordPress\/?p=147"},"modified":"2021-11-25T15:54:55","modified_gmt":"2021-11-25T06:54:55","slug":"reinvestigation-of-the-biomimetic-cyclization-of-35-diketoesters-application-to-the-total-synthesis-of-cyercene-a-an-%ce%b1-methoxy-%ce%b3-pyrone-containing-polypropionate","status":"publish","type":"post","link":"http:\/\/achem.okayama-u.ac.jp\/bioorgchem\/archives\/147","title":{"rendered":"Reinvestigation of the Biomimetic Cyclization of 3,5-Diketoesters: Application to the Total Synthesis of Cyercene A, an \u03b1-Methoxy-\u03b3-Pyrone-Containing Polypropionate"},"content":{"rendered":"\n<p>Kai Onda, Ichiro Hayakawa, Akira Sakakura*<br><em>Synlett<\/em><strong>2017<\/strong>,&nbsp;<em>28<\/em>&nbsp;(13), 1596\u20131600. &nbsp;(Published online: Apr 26, 2017)<br><a href=\"https:\/\/doi.org\/10.1055\/s-0036-1588795\">DOI: 10.1055\/s-0036-1588795&nbsp;<img decoding=\"async\" src=\"http:\/\/www.cc.okayama-u.ac.jp\/~sakakura\/bioorgchem\/_src\/9142\/img20180629093542651479.png\" alt=\"LinkIcon\"><\/a><\/p>\n\n\n\n<figure class=\"wp-block-image size-full\"><img loading=\"lazy\" decoding=\"async\" width=\"500\" height=\"176\" src=\"http:\/\/achem.okayama-u.ac.jp\/bioorgchem\/WordPress\/wp-content\/uploads\/2021\/07\/gamma-pyrone.png\" alt=\"\" class=\"wp-image-148\" srcset=\"http:\/\/achem.okayama-u.ac.jp\/bioorgchem\/WordPress\/wp-content\/uploads\/2021\/07\/gamma-pyrone.png 500w, http:\/\/achem.okayama-u.ac.jp\/bioorgchem\/WordPress\/wp-content\/uploads\/2021\/07\/gamma-pyrone-300x106.png 300w\" sizes=\"auto, (max-width: 500px) 100vw, 500px\" \/><\/figure>\n\n\n\n<p>The biomimetic cyclization of 3,5-diketoesters was reinvestigated for the synthesis of \u03b1-methoxy-\u03b3-pyrones. &nbsp;3,5-Diketoesters were selectively synthesized via the aldol reaction of commercially available methyl 2-methyl-3-oxopentanoate with an aldehyde followed by the oxidation with AZADOL\u00ae and PhI(OAc)2. &nbsp;The DBU-promoted intramolecular transesterification of 3,5-diketoesters showed excellent reactivity in MeOH, to give the corresponding \u03b3-hydroxy-\u03b1-pyrones in high yields under mild reaction conditions. &nbsp;Based on the present cyclization scheme, the total synthesis of cyercene A was achieved.<\/p>\n","protected":false},"excerpt":{"rendered":"<p>Kai Onda, Ichiro Hayakawa, Akira Sakakura*Synlett2017,&nbsp;28&nbsp;(13), 1596\u20131600. &nbsp;(Published online:  [&hellip;]<\/p>\n","protected":false},"author":1,"featured_media":148,"comment_status":"closed","ping_status":"closed","sticky":false,"template":"","format":"standard","meta":{"vkexunit_cta_each_option":"","footnotes":""},"categories":[6],"tags":[],"class_list":["post-147","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\/147","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=147"}],"version-history":[{"count":2,"href":"http:\/\/achem.okayama-u.ac.jp\/bioorgchem\/wp-json\/wp\/v2\/posts\/147\/revisions"}],"predecessor-version":[{"id":254,"href":"http:\/\/achem.okayama-u.ac.jp\/bioorgchem\/wp-json\/wp\/v2\/posts\/147\/revisions\/254"}],"wp:featuredmedia":[{"embeddable":true,"href":"http:\/\/achem.okayama-u.ac.jp\/bioorgchem\/wp-json\/wp\/v2\/media\/148"}],"wp:attachment":[{"href":"http:\/\/achem.okayama-u.ac.jp\/bioorgchem\/wp-json\/wp\/v2\/media?parent=147"}],"wp:term":[{"taxonomy":"category","embeddable":true,"href":"http:\/\/achem.okayama-u.ac.jp\/bioorgchem\/wp-json\/wp\/v2\/categories?post=147"},{"taxonomy":"post_tag","embeddable":true,"href":"http:\/\/achem.okayama-u.ac.jp\/bioorgchem\/wp-json\/wp\/v2\/tags?post=147"}],"curies":[{"name":"wp","href":"https:\/\/api.w.org\/{rel}","templated":true}]}}