期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 88, 期 4, 页码 2158-2165出版社
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.2c02564
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This article presents a concise approach to the synthesis of lysergic acid using simple aromatic precursors. The strategy involves coupling, dearomatization, and cyclization reactions, leading to the synthesis of a novel neuroactive compound, 12-chlorolysergic acid, in just 6 steps from commercially available starting materials. The use of dearomative retrosynthetic analysis offers important advantages in this design.
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.
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