Achiral auxiliary-assisted chiral transfer via microwave-accelerated aza-Claisen rearrangement: a short synthesis of (+)-1-hydroxyquinolizidinone

A short and efficient synthesis of (+)-1-hydroxyquinolizidinone as an advanced core intermediate for the syntheses of (+)-epiquinamide, (+)-homopumiliotoxin, and (+)-lupinine is described. The key feature of our strategy includes a sequential chiral transfer using an achiral phenylsulfide auxiliary...

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Bibliographic Details
Published in:Tetrahedron letters 2012-09, Vol.53 (36), p.4813-4815
Main Authors: Sim, Jaehoon, Yun, Hwayoung, Jung, Jong-Wha, Lee, Sujin, Kim, Nam-Jung, Suh, Young-Ger
Format: Article
Language:English
Subjects:
(+)-1-Hydroxyquinolizidinone
Achiral auxiliary
aza-Claisen rearrangement
Quinolizidine alkaloid
Transannulation
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Summary:A short and efficient synthesis of (+)-1-hydroxyquinolizidinone as an advanced core intermediate for the syntheses of (+)-epiquinamide, (+)-homopumiliotoxin, and (+)-lupinine is described. The key feature of our strategy includes a sequential chiral transfer using an achiral phenylsulfide auxiliary via microwave-accelerated aza-Claisen rearrangement of the unexplored N-thiophenoxyacetyl-α-vinyl piperidine substrate and the oxone-induced transannulation.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2012.06.073