A Concise Route to Dihydrobenzo[b]furans: Formal Total Synthesis of (+)-Lithospermic Acid
A Concise Route to Dihydrobenzo[b]furans: Formal Total Synthesis of (+)-Lithospermic Acid
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DOI：
10.1021/ol201130h
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发表时间：
2011-07-01
期刊：
影响因子：
5.2
通讯作者：
Coster, Mark J.
中科院分区：
文献类型：
--
作者：
Fischer, Joshua;Savage, G. Paul;Coster, Mark J.
Sonogashira偶联、Pd（II）催化的羰基化成环和苯并呋喃还原（Mg、MeOH、NH（4）Cl）的序列提供了反式-2-芳基-2，3-二氢苯并[B]呋喃-3-羧酸酯的收敛和模块化合成路线，其是许多生物活性天然产物的结构特征。将该方法应用于抗HIV天然产物（+）-紫草酸的全合成。
A sequence of Sonogashira coupling, Pd(II)-catalyzed carbonylative annulation, and benzofuran reduction (Mg, MeOH, NH(4)Cl) provides a convergent and modular synthetic route to trans-2-aryl-2,3-dihydrobenzo[b]furan-3-carboxylates, which are a structural feature of numerous biologically active natural products. This versatile strategy was applied to the formal total synthesis of the anti-HIV natural product (+)-lithospermic acid.