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Solving a Mystery with Classical and Dual Photoredox Catalysis: Application of Nickel in the Synthesis of Ergot Alkaloids
Organic Letters ( IF 5.2 ) Pub Date : 2024-05-10 , DOI: 10.1021/acs.orglett.4c01291
Jan Brauer 1 , Rainer Wiechert 1 , Anika Hahn 1 , Till Opatz 1
Affiliation  

A short synthesis of the ergot alkaloid lysergene and a formal total synthesis of lysergic acid diethylamide (LSD) under the avoidance of palladium and including two nickel-catalyzed steps instead have been developed. A key intermediate of this approach has already been reported by Hendrickson et al. in 2004 (Hendrickson, J.B. et al. Org. Lett. 2004, 6, 3–5), yet the spectral data do not match, adding to doubts about the course of their route. While the final steps of the Hendrickson synthesis could not be reproduced, we were able to leverage the elusive intermediate.

中文翻译:


用经典和双重光氧化还原催化解开谜团:镍在麦角生物碱合成中的应用



麦角生物碱麦角碱的简短合成和麦角酸二乙酰胺 (LSD) 的正式全合成已经开发出来,该全合成避免使用钯,并包括两个镍催化步骤。 Hendrickson 等人已经报道了这种方法的关键中间体。 2004 年(Hendrickson, J.B. et al. Org. Lett. 2004, 6, 3-5),但光谱数据不匹配,增加了对其路线的怀疑。虽然亨德里克森合成的最后步骤无法重现,但我们能够利用难以捉摸的中间体。
更新日期:2024-05-10
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