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Synfacts 2021; 17(11): 1267
DOI: 10.1055/s-0040-1720735
Chemistry in Medicine and Biology

An Asymmetric [3+2] Cycloaddition/Ring-Expansion Sequence Towards Lysergic Acid

Contributor(s):
Dirk Trauner
,
Klaus-Peter Ruehmann
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
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Key words

1,3-dipolar cycloaddition - Oppolzer’s auxiliary - Cossy–Charette ring expansion

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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