Rapid Syntheses of (?)‐FR901483 and (+)‐TAN1251C Enabled by Complexity‐Generating Photocatalytic Olefin Hydroaminoalkylation

Reich Dominik; Trowbridge Aaron; Gaunt Matthew J.

摘要

Abstract > We report a common strategy to facilitate the syntheses of the polycyclic alkaloids (?)‐FR901483 ( 1 ) and (+)‐TAN1251C ( 2 ). A divergent synthetic strategy provides access to both natural products through a pivotal spirolactam intermediate ( 3 ), which can be accessed on a gram‐scale. A photocatalytic olefin hydroaminoalkylation brings together three readily available building blocks and forges the majority of the carbon framework present in 1 and 2 in a single operation, leading to concise total syntheses. The complexity‐generating photocatalytic process also provides direct access to novel non‐racemic spirolactam scaffolds that are likely to be of interest to early‐stage drug discovery programs. </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> > 我们报告了一种普遍的策略，以促进多环生物碱（α）的合成 - FR901483（ 1 </ b> ）和（+） - Tan1251C（ 2 </ b> ）。发散的合成策略通过枢轴螺酰胺中间体提供对天然产物的访问（ 3 </ b> ），可以在革兰氏级上访问。光催化烯烃羟氨基甲基化带来了三个容易获得的建筑物，并造成了存在的大部分碳框架 1 </ b> 和 2 </ b> 在单一的操作中，导致简洁的总合成。复杂性的光催化过程还提供了对早期药物发现计划可能感兴趣的新型非外消旋螺旋酰胺支架的直接进入。 </ 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6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=Reich Dominik&option=202" target="_blank" rel="nofollow">Reich Dominik;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Trowbridge Aaron&option=202" target="_blank" rel="nofollow">Trowbridge Aaron;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Gaunt Matthew J.&option=202" target="_blank" rel="nofollow">Gaunt Matthew J.;</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>Department of ChemistryUniversity of CambridgeLensfield Road Cambridge CB2 1EW UK;</p> <p>Department of ChemistryUniversity of CambridgeLensfield Road Cambridge CB2 1EW UK;</p> <p>Department of ChemistryUniversity of CambridgeLensfield Road Cambridge CB2 1EW UK;</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=amine synthesis&option=203" rel="nofollow">amine synthesis;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=medicinal chemistry&option=203" rel="nofollow">medicinal chemistry;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=total synthesis&option=203" rel="nofollow">total synthesis;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=photoredox chemistry&option=203" rel="nofollow">photoredox chemistry;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=radical chemistry&option=203" rel="nofollow">radical chemistry;</a> </p> <div class="translation"> 机译：胺合成;药物化学;总合成;Photoreox化学;激进的化学; 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