Total synthesis of 3-epi-(+)-lycoricidine from Garner aldehyde via intramolecular aldol cyclization

[Display omitted] A highly efficient total synthesis of 3-epi-(+)-lycoricidine has been described for the first time from easily available (S)-Garner aldehyde with an overall yield of 7% in 20 steps. Stereoselective nucleophilic addition, Sharpless asymmetric dihydroxylation, Dess–Martin periodinane...

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Bibliographic Details
Published in:Tetrahedron letters 2015-01, Vol.56 (1), p.146-149
Main Authors: Bera, Saurav, Das, Sanjit Kumar, Saha, Tiash, Panda, Gautam
Format: Article
Language:English
Subjects:
Aldehydes
Aldol cyclization
Asymmetry
Garner aldehyde
Lycoricidine
Oxidation
Reduction
Synthesis (chemistry)
Tetrahedrons
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Summary:[Display omitted] A highly efficient total synthesis of 3-epi-(+)-lycoricidine has been described for the first time from easily available (S)-Garner aldehyde with an overall yield of 7% in 20 steps. Stereoselective nucleophilic addition, Sharpless asymmetric dihydroxylation, Dess–Martin periodinane oxidation, intramolecular aldol cyclization, and Luche reduction are the salient features of this approach.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2014.11.045