AI Article Synopsis
- The synthesis of (+)-euphococcinine and (-)-adaline, two alkaloids with a unique quaternary carbon-nitrogen structure, is explored.
- Key synthetic techniques include a 3,3-sigmatropic rearrangement for creating an all-carbon quaternary center and a ring-closing alkene metathesis to form an 8-membered ring.
- The process utilizes a single enantiomer of p-menthane-3-carboxaldehyde to produce two alkaloids that have opposite configurations.
Article Abstract
We describe the syntheses of (+)-euphococcinine and (-)-adaline, two naturally occurring alkaloids containing a quaternary carbon bearing a nitrogen atom. Key features of the syntheses are a 3,3-sigmatropic rearrangement to give an all-carbon quaternary center, a ring-closing alkene metathesis to give an 8-membered ring, and the use of a single enantiomer of p-menthane-3-carboxaldehyde to make two natural alkaloids of opposite configuration.
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| http://dx.doi.org/10.1021/jo9001992 | DOI Listing |
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