Development of a Cross‐Conjugated Vinylogous [4+2] Anionic Annulation and Application to the Total Synthesis of Natural Antibiotic (±)‐ABX

Huang Jing‐Kai; Shia Kak‐Shan

摘要

Abstract >The cross‐conjugated vinylogous [4+2] anionic annulation has been newly developed, the cascade process of which has a high preference for regiochemical control and chemoselectivity, giving rise to exclusively Michael‐type adducts in moderate to high yields (up to 94?%, 35 examples). By making use of this approach as a key operation, the first total synthesis of natural antibiotic ABX, in racemic form, has been successfully achieved in a concise 7‐step sequence with an overall yield of about 20?%. </abstract> </span> <span class="z_kbtn z_kbtnclass hoverxs" style="display: none;">展开▼</span> </div> <div class="translation abstracttxt"> <span class="zhankaihshouqi fivelineshidden" id="abstract"> <span>机译：</span><Abstract Type =“Main”XML：Lang =“en”> <标题类型=“main”>抽象</ title> >已经新开发了交叉共轭的乙烯基[4 + 2]阴离子环状，其级联方法具有高偏好对调节控制和化学选择性，从而产生了中等至高收益率的完全迈克尔型加合物（UP 到94？％，35个例子）。通过利用这种方法作为关键操作，在简洁的7步骤序列中，以外消旋形式的自然抗生素ABX的第一总合成已经成功地实现了约20μm的总收率。</ p> </摘要> </span> <span class="z_kbtn z_kbtnclass hoverxs" style="display: none;">展开▼</span> </div> </div> <div class="record"> <h2 class="all_title" id="enpatent33" >著录项</h2> <ul> <li> <span class="lefttit">来源</span> <div style="width: 86%;vertical-align: text-top;display: inline-block;"> <a href='/journal-foreign-19011/'>《Angewandte Chemie》</a> <b style="margin: 0 2px;">|</b><span>2020年第16期</span><b style="margin: 0 2px;">|</b><span>共6页</span> </div> </li> <li> <div class="author"> <span class="lefttit">作者</span> <p id="fAuthorthree" class="threelineshidden zhankaihshouqi"> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Huang Jing‐Kai&option=202" target="_blank" rel="nofollow">Huang Jing‐Kai;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Shia Kak‐Shan&option=202" target="_blank" rel="nofollow">Shia Kak‐Shan;</a> </p> <span class="z_kbtnclass z_kbtnclassall hoverxs" id="zkzz" style="display: none;">展开▼</span> </div> </li> <li> <div style="display: flex;"> <span class="lefttit">作者单位</span> <div style="position: relative;margin-left: 3px;max-width: 639px;"> <div class="threelineshidden zhankaihshouqi" id="fOrgthree"> <p>Institute of Biotechnology and Pharmaceutical ResearchNational Health Research Institutes35 Keyan Road Zhunan Miaoli County 35053 Taiwan R.O.C.;</p> <p>Institute of Biotechnology and Pharmaceutical ResearchNational Health Research Institutes35 Keyan Road Zhunan Miaoli County 35053 Taiwan R.O.C.;</p> </div> <span class="z_kbtnclass z_kbtnclassall hoverxs" id="zhdw" style="display: none;">展开▼</span> </div> </div> </li> <li > <span class="lefttit">收录信息</span> <span style="width: 86%;vertical-align: text-top;display: inline-block;"></span> </li> <li> <span class="lefttit">原文格式</span> <span>PDF</span> </li> <li> <span class="lefttit">正文语种</span> <span>eng</span> </li> <li> <span class="lefttit">中图分类</span> <span><a href="https://www.zhangqiaokeyan.com/clc/1188.html" title="应用化学">应用化学;</a></span> </li> <li class="antistop"> <span class="lefttit">关键词</span> <p style="width: 86%;vertical-align: text-top;"> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=acceptor&option=203" rel="nofollow">acceptor;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=anionic annulation&option=203" rel="nofollow">anionic annulation;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=benzylogous&option=203" rel="nofollow">benzylogous;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=donor&option=203" rel="nofollow">donor;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=vinylogous&option=203" rel="nofollow">vinylogous;</a> </p> <div class="translation"> 机译：接受者;阴离子环化;苄基吉祥;捐赠者;乙烯基; </div> </li> </ul> </div> </div> <div class="literature cardcommon"> <div class="similarity "> <h3 class="all_title" id="enpatent66">相似文献</h3> <div class="similaritytab clearfix"> <ul> <li class="active" >外文文献</li> <li >中文文献</li> <li >专利</li> </ul> </div> <div class="similarity_details"> <ul > <li> <div> <b>1. </b><a class="enjiyixqcontent" href="/journal-foreign-detail/0704028160759.html">Development of a Cross‐Conjugated Vinylogous [4+2] Anionic Annulation 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PHARMACOKINETIC PROPERTIES, OF POLYMIXINS, NATURAL OCTAPEPTINS AND THEIR DERIVATIVES; METHOD FOR THE AWARENESS OF CLINICALLY IMPORTANT GRAM-NEGATIVE BACTERIA TO A DEFENSE MECHANISM COMPLEMENT IN THE SERUM; USE OF A DERIVATIVE; AND PROCESS FOR THE PREPARATION OF A POLYMIXIN DERIVATIVE OF FORMULA (I)</a> <b>[P]</b> . <span> 外国专利：  NO341982B1 </span> <span> . 2018-03-05</span> </div> <p class="zwjiyix translation" style="max-width: initial;height: auto;word-break: break-all;white-space: initial;text-overflow: initial;overflow: initial;"> <span>机译：一般配方的多聚新霉素衍生物（I）;组合产品;药物成分;革兰氏阴性菌引起的患者感染的治疗，缓解或改善的方法;将革兰氏阴性细菌敏化为抗菌剂的方法;开发未发表的抗生素的方法;在个体感染治疗中降低多粘菌素，天然八肽及其衍生物毒性的方法;改善多聚体，天然螯合剂及其衍生物的药动学性质的方法;认识临床上重要的革兰氏阴性细菌对血清中防御机制的补充;使用衍生词;的多聚新霉素衍生物的制备和方法（I） </span> </p> </li> <li> <div> <b>2. </b><a class="enjiyixqcontent" href="/patent-detail/06130420374031.html">POLYMIXIN DERIVATIVE OF THE GENERAL FORMULA (I); COMBINATION PRODUCT; PHARMACEUTICAL COMPOSITION; METHOD FOR THE TREATMENT, RELIEF OR IMPROVEMENT OF AN INFECTION, IN A PATIENT, CAUSED BY A GRAM-NEGATIVE BACTERIA; METHOD FOR SENSITIZING GRAM-NEGATIVE BACTERIA TO AN ANTIBACTERIAL AGENT; METHOD FOR THE DEVELOPMENT OF UNPUBLISHED ANTIBIOTICS; METHODS FOR REDUCING THE TOXICITY OF POLYMIXINS, NATURAL OCTAPEPTINS AND THEIR DERIVATIVES DURING THE APPLICATION OF THE SAME IN THE TREATMENT OF INFECTIONS IN AN INDIVIDUAL; METHOD TO IMPROVE PHARMACOKINETIC PROPERTIES, OF POLYMIXINS, NATURAL OCTAPEPTINS AND THEIR DERIVATIVES; METHOD FOR THE AWARENESS OF CLINICALLY IMPORTANT GRAM-NEGATIVE BACTERIA TO A DEFENSE MECHANISM COMPLEMENT IN THE SERUM; USE OF A DERIVATIVE; AND PROCESS FOR THE PREPARATION OF A POLYMIXIN DERIVATIVE OF FORMULA (I)</a> <b>[P]</b> . <span> 外国专利：  BRPI0715095A2 </span> <span> . 2013-10-15</span> </div> <p class="zwjiyix translation" style="max-width: initial;height: auto;word-break: break-all;white-space: initial;text-overflow: initial;overflow: initial;"> <span>机译：一般配方的多聚新霉素衍生物（I）;组合产品;药物成分;革兰氏阴性菌引起的患者感染的治疗，缓解或改善的方法;将革兰氏阴性细菌敏化为抗菌剂的方法;开发未发表的抗生素的方法;在个体感染治疗中降低多粘菌素，天然八肽及其衍生物毒性的方法;改善多聚体，天然螯合剂及其衍生物的药动学性质的方法;认识临床上重要的革兰氏阴性细菌对血清中防御机制的补充;使用衍生词;的多聚新霉素衍生物的制备和方法（I） </span> </p> </li> <li> <div> <b>3. </b><a class="enjiyixqcontent" href="/patent-detail/06130430268208.html">POLYMIXIN DERIVATIVE OF THE GENERAL FORMULA (I); COMBINATION PRODUCT; PHARMACEUTICAL COMPOSITION; METHOD FOR THE TREATMENT, RELIEF OR IMPROVEMENT OF AN INFECTION, IN A PATIENT, CAUSED BY A GRAM-NEGATIVE BACTERIA; METHOD FOR SENSITIZING GRAM-NEGATIVE BACTERIA TO AN ANTIBACTERIAL AGENT; METHOD FOR THE DEVELOPMENT OF UNPUBLISHED ANTIBIOTICS; METHODS FOR REDUCING THE TOXICITY OF POLYMIXINS, NATURAL OCTAPEPTINS AND THEIR DERIVATIVES DURING THE APPLICATION OF THE SAME IN THE TREATMENT OF INFECTIONS IN AN INDIVIDUAL; METHOD TO IMPROVE PHARMACOKINETIC PROPERTIES, OF POLYMIXINS, NATURAL OCTAPEPTINS AND THEIR DERIVATIVES; METHOD FOR THE AWARENESS OF CLINICALLY IMPORTANT GRAM-NEGATIVE BACTERIA TO A DEFENSE MECHANISM COMPLEMENT IN THE SERUM; USE OF A DERIVATIVE; AND PROCESS FOR THE PREPARATION OF A POLYMIXIN DERIVATIVE OF FORMULA (I)</a> <b>[P]</b> . <span> 外国专利：  NO20090674L </span> <span> . 2009-05-08</span> </div> <p class="zwjiyix translation" style="max-width: initial;height: auto;word-break: break-all;white-space: initial;text-overflow: initial;overflow: initial;"> <span>机译：一般配方的多聚新霉素衍生物（I）;组合产品;药物成分;革兰氏阴性菌引起的患者感染的治疗，缓解或改善的方法;将革兰氏阴性细菌敏化为抗菌剂的方法;开发未发表的抗生素的方法;在个体感染治疗中降低多粘菌素，天然八肽及其衍生物毒性的方法;改善多聚体，天然螯合剂及其衍生物的药动学性质的方法;认识临床重要的革兰氏阴性细菌对血清中防御机制的补充;使用衍生词;的多聚新霉素衍生物的制备和方法（I） </span> </p> </li> </ul> </div> </div> </div> <div class="theme cardcommon" style="overflow: auto;display:none"> <h3 class="all_title" id="enpatent55">相关主题</h3> <ul id="subject"> </ul> </div> </div> </div> </div> <div class="right rightcon"> <div class="details_img cardcommon clearfix" style="margin-bottom: 10px;display:none;" > </div> </div> </div> <div id="thesis_get_original1" class="downloadBth" 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