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Synfacts 2021; 17(11): 1267
DOI: 10.1055/s-0040-1720735
DOI: 10.1055/s-0040-1720735
Chemistry in Medicine and Biology
An Asymmetric [3+2] Cycloaddition/Ring-Expansion Sequence Towards Lysergic Acid
Rathnayake U,
Garner P.
*
Washington State University, Pullman, USA
Asymmetric Synthesis of Lysergic Acid via an Intramolecular (3+2) Dipolar Cycloaddition/Ring-Expansion Sequence.
Org. Lett. 2021;
23: 6756-6759
DOI: 10.1021/acs.orglett.1c02337.
Asymmetric Synthesis of Lysergic Acid via an Intramolecular (3+2) Dipolar Cycloaddition/Ring-Expansion Sequence.
Org. Lett. 2021;
23: 6756-6759
DOI: 10.1021/acs.orglett.1c02337.
Significance
Amide derivatives of lysergic acid have been investigated for the treatment of various neurological disorders. While many syntheses of lysergic acid itself have been disclosed previously, Rathnayake and Garner describe a new strategy to afford the enantiopure piperidine core.
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Comment
Using Oppolzer’s camphorsultam auxiliary, an intramolecular 1,3-dipolar cycloaddition of the in situ generated azomethine ylide and the alkyne established an enantiopure dihydropyrrole. A subsequent aziridinium-mediated ring expansion then afforded the piperidine core of lysergic acid.
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Publication History
Article published online:
19 October 2021
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