Total synthesis of (−)-δ-lycorane

The total synthesis of (−)-δ-lycorane is reported. We performed organocatalytic Mannich reaction between phenylacetaldehyde and γ-hydroxy lactam to construct a 5-substituted-2-pyrrolidone derivative in favor of the cis -isomer. Furthermore, diastereoselective conjugate addition to α,β-unsaturated la...

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Bibliographic Details
Published in:New journal of chemistry 2023-10, Vol.47 (41), p.189-1894
Main Authors: Shukla, Jyoti, Gangwar, Manoj Kumar, Koley, Dipankar
Format: Article
Language:English
Subjects:
Amides
Chemical synthesis
Metathesis
Phenylacetaldehyde
Stereoselectivity
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Summary:The total synthesis of (−)-δ-lycorane is reported. We performed organocatalytic Mannich reaction between phenylacetaldehyde and γ-hydroxy lactam to construct a 5-substituted-2-pyrrolidone derivative in favor of the cis -isomer. Furthermore, diastereoselective conjugate addition to α,β-unsaturated lactam was accomplished to obtain 4,5-disubstituted-2-pyrrolidone. The other salient features of this synthesis include Bischler-Napieralski reaction and ring closing metathesis. The total synthesis of (−)-δ-lycorane is reported.
ISSN:1144-0546
1369-9261
DOI:10.1039/d3nj03567k