Six-Step Synthesis of (±)-Lysergic Acid
Six-Step Synthesis of (±)-Lysergic Acid
复制标题
(±)-麦角酸的六步合成
DOI：
10.1021/acs.joc.2c02564
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发表时间：
2023
期刊：
影响因子：
--
通讯作者：
Smith, Joel M.
中科院分区：
文献类型：
--
作者：
Knight, Brian J.;Harbit, Ryan C.;Smith, Joel M.
本文介绍了一种由简单芳香族前体合成麦角酸的简便方法。成功的策略依赖于从商业起始原料在6个总合成步骤中的卤代吡啶与4-卤代吲哚衍生物的偶联、脱芳构化和环化。除了突出采用脱芳香逆合成分析的优点之外，该设计是实用的，并且预期能够合成新的神经活性化合物，例如合成新的天然产物衍生物12-氯麦角酸。
This article describes a concise synthesis of lysergic acid from simple aromatic precursors. The successful strategy relies on the coupling, dearomatization, and cyclization of a halopyridine with a 4-haloindole derivative in 6 total synthetic steps from commercial starting materials. In addition to highlighting the advantages of employing dearomative retrosynthetic analysis, the design is practical and anticipated to enable the synthesis of novel neuroactive compounds as exemplified by the synthesis of a novel natural product derivative, 12-chlorolysergic acid.